N-phenyl-maleimides and herbicidal and plant growth regulating methods of use thereof

ABSTRACT

Novel derivatives of N-phenylmaleic acid imide and N-phenylsuccinimide have good pre- and post-emergence selective herbicidal properties and they influence plant growth. The compounds correspond to the formula I ##STR1## in which |: represent a single or double bond, 
     R 1  represents hydrogen or fluorine, 
     R 2  represents halogen, 
     Y represents C 1  -C 8  -alkyl, 
     Z represents hydrogen or C 1  -C 8  -alkyl, and 
     A represents hydrogen or a group ##STR2## wherein R 3 , R 4 , R 5 , R 6 , R 7  and R 8  represent customary organic radicals and X represents oxygen, sulphur, SO, SO 2 , NH, alkylimino or alkenylimino.

The present invention relates to novel derivatives of N-phenyl-maleimideand N-phenyl-succinimide having a herbicidal and plant growth regulatingaction, to agrochemical compositions containing these substances asactive ingredients, to the use of the novelN-phenyl-tetrahydrophthalimides for the selective control of weeds orfor regulating plant growth, and to processes for the preparation ofthese novel compounds. The invention relates also to novel intermediatesused for the preparation of the novel active ingredients.

The novel derivatives of N-phenylmaleimide and N-phenylsuccinimidecorrespond to the formula I ##STR3## in which |: represents a single ordouble bond,

R¹ represents hydrogen or fluorine,

R² represents halogen,

Y represents C₁ -C₈ -alkyl,

Z represents hydrogen or C₁ -C₈ -alkyl, and

A represents hydrogen or a group ##STR4## wherein R³ representshydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -haloalkyl,

R⁴ represents hydrogen, C₁ -C₈ -alkyl, C₂ -C₈ -alkoxyalkyl, C₂ -C₈-alkylthioalkyl, C₂ -C₈ -alkylaminoalkyl, C₁ -C₈ -haloalkyl, C₁ -C₈-cyanoalkyl, C₃ -C₈ -alkenyl, C₃ -C₈ -haloalkenyl, C₃ -C₈ -alkynyl, C₃-C₇ -cycloalkyl, C₃ -C₇ -halocycloalkyl, C₁ -C₄ -alkylsulphonyl, asodium ion, a potassium ion, a magnesium ion, a calcium ion, an ammoniumion, C₁ -C₄ -alkoxycarbonyl, benzyloxycarbonyl, C₅ -C₇-cycloalkoxycarbonyl, phenoxycarbonyl which is unsubstituted ormono-substituted at the phenyl ring by halogen, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkyl, cyano or by nitro, or represents C₁ -C₄-alkylthiocarbonyl, C₁ -C₄ -alkylaminocarbonyl, dimethylaminocarbonyl,benzylaminocarbonyl, C₃ -C₇ -cycloalkylaminocarbonyl,phenylaminocarbonyl which is unsubstituted or mono-substituted at thephenyl nucleus by halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkyl, cyano or by nitro, or represents C₁ -C₈ -alkylcarbonyl,allylcarbonyl, benzylcarbonyl which is unsubstituted or mono-substitutedat the phenyl ring by halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkyl, cyano or by nitro, or represents C₃ -C₇ -cycloalkylcarbonyl,benzoyl which is unsubstituted or mono-substituted at the phenyl ring byhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, cyano or bynitro, or represents furoyl or thenoyl; or represents C₁ -C₄ -alkylsubstituted by phenyl, halophenyl, C₁ -C₄ -alkylphenyl, C₁ -C₄-alkoxyphenyl, C₁ -C₄ -haloalkylphenyl, C₁ -C₄ -haloalkoxyphenyl,nitrophenyl, cyanophenyl, C₁ -C₈ -alkoxycarbonyl, C₂ -C₈-alkoxyalkoxycarbonyl, C₃ -C₈ -alkenyloxycarbonyl, C₃ -C₈-alkynyloxycarbonyl, C₁ -C₈ -alkylthiocarbonyl, C₃ -C₈-alkenylthiocarbonyl, C₃ -C₈ -alkynylthiocarbonyl, carbamoyl, C₁ -C₄-alkylaminocarbonyl, di-C₁ -C₄ -alkylaminocarbonyl, phenylaminocarbonylwhich is unsubstituted or mono-substituted at the phenyl ring byhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, cyano, nitro or by C₁ -C₄-haloalkyl; dioxolan-2-yl which is unsubstituted or substituted by oneor two C₁ -C₄ -alkyl radicals; or 1,3-dioxan-2-yl which is unsubstitutedor substituted by one or two C₁ -C₄ -alkyl radicals;

R⁵ and R⁶ represents, independently of the other, C₁ -C₄ -alkyl, C₂ -C₄-haloalkyl or C₂ -C₈ -alkoxyalkyl, or

R⁵ and R⁶ together represent an ethylene or propylene bridge or a1,2-cyclohexanylene body, these groups being unsubstituted orsubstituted by one or two radicals selected from the group comprising C₁-C₄ -alkyl, C₁ -C₄ -haloalkyl and C₁ -C₄ -hydroxyalkyl,

R⁷ represents hydroxy, C₁ -C₈ -alkoxy, C₂ -C₈ -alkoxyalkoxy, C₂ -C₈-alkylthioalkoxy, C₂ -C₈ -alkylaminoalkoxy, C₁ -C₈ -cyanoalkoxy, C₃ -C₈-alkenyloxy, C₂ -C₈ -haloalkenyloxy, C₃ -C₈ -alkynyloxy, C₃ -C₇-cycloalkoxy, C₃ -C₇ -halocycloalkoxy, benzyloxy which is unsubstitutedor mono-substituted at the phenyl nucleus by halogen, C₁ -C₄ -alkyl, C₁-C₄ -alkoxy, C₁ -C₄ -haloalkyl, cyano or by nitro, or representsphenoxy, halophenoxy, C₁ -C₄ -alkylphenoxy, C₁ -C₄ -alkoxyphenoxy, C₁-C₄ -haloalkylphenoxy, cyanophenoxy, nitrophenoxy, phenylthio,halophenylthio, C₁ -C₄ -alkylphenylthio, C₁ -C₄ -alkoxyphenylthio, C₁-C₄ -haloalkylthio, cyanophenylthio, nitrophenylthio, the salt groups,--O--Na, --O--K, --O--Ca, --O--Mg, --O--NH₄ ; amino, C₁ -C₄ -alkylamino,di-C₁ -C₄ -alkylamino, C₂ -C₄ -haloalkylamino, di-C₂ -C₄-haloalkylamino, C₁ -C₄ -hydroxyalkylamino, di-C₁ - C₄-hydroxyalkylamino, C₃ -C₄ -alkenylamino, diallylamino, -N-pyrrolidino,-N-piperidino, -N-morpholino, -N-thiomorpholino, -N-piperidazino, C₁ -C₈-alkylthio, C₃ -C₈ -alkenylthio, benzylthio, C₁ -C₄ -alkylthiosubstituted by C₁ -C₈ -alkoxycarbonyl, C₂ -C₈ -alkoxyalkoxycarbonyl, C₃-C₈ -alkenyloxycarbonyl, C₃ -C₈ -alkynyloxycarbonyl, C₁ -C₈-alkylthiocarbonyl, C₃ -C₈ -alkenylthiocarbonyl or by C₃ -C₈-alkynylthiocarbonyl; or C₁ -C₄ -alkoxy substituted by C₁ -C₈-alkoxycarbonyl, C₂ -C₈ -alkoxyalkoxycarbonyl, C₃ -C₈-alkenyloxycarbonyl, C₃ -C₈ -alkynyloxycarbonyl, C₁ -C₈-alkylthiocarbonyl, C₃ -C₈ -alkenylthiocarbonyl, C₃ -C₈-alkynylthiocarbonyl, C₁ -C₄ -alkylaminocarbonyl, di-C₁ -C₄-alkylaminocarbonyl or by phenylaminocarbonyl which is unsubstituted ormono-substituted at the phenyl nucleus by halogen, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, C₁ -C₄ -haloalkyl, cyano or by nitro;

X represents oxygen, sulphur, --SO--, --SO₂ --, --NH--, -N(C₁ -C₄-alkyl)- or -N(C₃ -C₄ -alkenyl)-, and

R⁸ represents C₁ -C₈ -alkyl, C₂ -C₈ -alkoxyalkyl, C₂ -C₈-alkylthioalkyl, C₂ -C₈ -alkylaminoalkyl, C₂ -C₈ -haloalkyl, C₁ -C₈-cyanoalkyl, C₃ -C₈ -alkenyl, C₂ -C₈ -haloalkenyl, C₃ -C₈ -alkynyl, C₃-C₇ -cycloalkyl, C₃ -C₇ -halocycloalkyl, C₁ -C₈ -alkylcarbonyl,allylcarbonyl, benzylcarbonyl which is unsubstituted or mono-substitutedat the phenyl ring by halogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkyl, cyano or by nitro, or represents C₃ -C₇ -cycloalkylcarbonyl,benzoyl which is unsubstituted or mono-substituted at the phenyl ring byhalogen, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁ -C₄ -haloalkyl, cyano or bynitro, or represents furoyl or thienoyl, or C₁ -C₄ -alkyl substituted byphenyl, halophenyl, C₁ -C₄ -alkylphenyl, C₁ -C₄ -alkoxyphenyl, C₁ -C₄-haloalkylphenyl, C₁ -C₄ -haloalkoxyphenyl, nitrophenyl, cyanophenyl, C₁-C.sub. 8 -alkoxycarbonyl, C₂ -C₈ -alkoxyalkoxycarbonyl, C₃ -C₈-alkenyloxycarbonyl, C₃ -C₈ -alkenylthiocarbonyl, C₁ -C₈-alkylthiocarbonyl, C₃ -C₈ -alkenylthiocarbonyl, C₃ -C₈-alkynylthiocarbonyl, carbamoyl, C₁ -C₄ -alkylaminocarbonyl, di-C₁ -C₄-alkylaminocarbonyl, or by phenylaminocarbonyl which is unsubstituted ormono-substituted at the phenyl ring by halogen, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, cyano, nitro or by C₁ -C₄ -haloalkyl; dioxolan-2-yl which isunsubstituted or substituted by one or two C₁ -C₄ -alkyl radicals; or1,3-dioxan-2-yl which is unsubstituted or substituted by one or two C₁-C₄ -alkyl radicals.

Derivatives of N-phenyl-2,3-dimethylmaleic acid imides are known asherbicides from the literature, from published Patent Applications DE-ANo. 2 735 841 or JA-A No. 57.144 204 and from U.S. Pat. No. 4,138,243.

In the above definitions, the generic terms given include, for example,the following specific individual substituents, but this list does notconstitute any limitation of the invention:

alkyl: methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec.-butyland tert.-butyl, preferably methyl and ethyl.

halogen: fluorine, chlorine, bromine and iodine, preferably fluorine,chlorine and bromine.

alkoxy: methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy,sec.-butoxy and tert.-butoxy, preferably methoxy or ethoxy.

haloalkyl: fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl,dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl,2-chloroethyl and 2,2,2-trichloroethyl, preferably chloromethyl,2-chloroethyl and trifluoromethyl.

haloalkoxy: fluoromethoxy, difluoromethoxy, trifluoromethoxy,2,2,2-trifluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2-fluoroethoxy,2-chloroethoxy and 2,2,2-trichloroethoxy, preferably difluoromethoxy,2-chloroethoxy and trifluoromethoxy.

alkoxycarbonyl: methoxycarbonyl, ethoxycarbonyl, 4-propoxycarbonyl,isopropoxycarbonyl and n-butoxycarbonyl, preferably methoxycarbonyl andethoxycarbonyl.

alkoxyalkyl: methoxymethyl, ethoxymethyl, propoxymethyl, methoxyethyl,ethoxyethyl, propoxyethyl, methoxypropyl, ethoxypropyl or propoxypropyl.

alkylthioalkyl: methylthiomethyl, ethylthiomethyl, methylthioethyl,ethylthioethyl or isopropylthioethyl.

alkylaminoalkyl: methylaminoethyl, dimethylaminoethyl, ethylaminoethylor diethylaminoethyl.

cyanoalkyl: cyanomethyl, cyanoethyl or cyanopropyl.

alkenyl: allyl, 2-butenyl, 3-butenyl or methallyl, but preferably allyl.

alkynyl: propargyl, 2-butynyl or 3-butynyl, but preferably propargyl.

cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl orcycloheptyl. Cyclopentyl or cyclohexyl is preferred.

halocycloalkyl: 2,2-dichlorocyclopropyl or pentachlorocyclohexyl.

alkylsulphonyl: methylsulphonyl, ethylsulphonyl, propylsulphonyl orbutylsulphonyl. Methyl- and ethylsulphonyl are preferred.

cycloalkoxycarbonyl: cyclopentyloxycarbonyl or cyclohexyloxycarbonyl.

phenyl, also as part of a larger substituent, such as phenoxy,phenylthio, phenoxycarbonyl, phenylaminocarbonyl, benzyl or benzoyl, maygenerally be unsubstituted or substituted by a further substituent. Thesubstituents may then be in the ortho-, meta- or para-position.Preferred substituent positions are the ortho- and para-position to thering linking site. Preferred substituents are halogen atoms.

In the further substituents that are composed of several basic elements,the partial elements have the meanings explained above by reference toexamples. These lists also do not represent in these cases anylimitation of the invention: they are of an illustrative nature.

Among the compounds according to the invention these are preferred

(a) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents C₁ -C₈ -alkyl,

Z represents hydrogen or C₁ -C₈ -alkyl,

A represents the radical --COR³, and

R³ represents hydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -haloalkyl;

(b) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents C₁ -C₈ -alkyl,

Z represents hydrogen or C₁ -C₈ -alkyl,

A represents the radical --CR³ ═NOR⁴, and

R³ and R⁴ are as defined under formula I;

(c) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents C₁ -C₈ -alkyl,

Z represents hydrogen or C₁ -C₈ -alkyl,

A represents the radical --C(CN)═NOR⁴, and

R⁴ is as defined under formula I;

(d) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents C₁ -C₈ -alkyl,

Z represents hydrogen or C₁ -C₈ -alkyl,

A represents the radical ##STR5## and R³, R⁵ and R⁶ are as defined underformula I;

(e) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents C₁ -C₈ -alkyl,

Z represents hydrogen or C₁ -C₈ -alkyl

A represents the radical --COR⁷, and

R⁷ is as defined under formula I;

(f) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents C₁ -C₈ -alkyl,

Z represents hydrogen or C₁ -C₈ -alkyl,

A represents the radical --XR⁸, and

X and R⁸ are as defined under formula I, specifically

N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2,3-dimethyl-maleic acid imide,

N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2-n-butyl-3-methyl-maleic acidimide and

N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2-ethyl-3-methyl maleic acidimide;

(g) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y and Z each represents methyl, and

A has one of the meanings given under formula I;

(h) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents ethyl,

Z represents methyl, and

A has one of the meanings given under formula I;

(i) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents isopropyl,

Z represents methyl, and

A has one of the meanings given under formula I;

(k) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents isopropyl,

Z represents hydrogen, and

A has one of the meanings given under formula I;

(l) the imides of the formula I in which

R¹ represents hydrogen or fluorine,

R² represents chlorine or bromine,

Y represents n-butyl,

Z represents methyl, and

A has one of the meanings given under formula I.

The compounds of the formula I are prepared according to the inventionby condensing a maleic anhydride or a succinic anhydride of the formulaII ##STR6## in which |: represents a single or double bond and Y and Zare as defined under formula I, with an aniline of the formula III##STR7## in which A, R¹ and R² are as defined under formula I.

The above condensation reaction is advantageously carried out in aninert organic solvent. The reaction temperature is generally betweenroom temperature and the boiling temperature of the reaction mixtureand, preferably, the reaction mixture is heated to the reflux. Thecondensation reaction can be accelerated by adding condensationcatalysts and removing the water reaction product formed. The sameeffect is achieved by adding water-removing agents, such as, forexample, sulphuric acid.

Suitable solvents are especially higher-boiling hydrocarbons, loweralkanecarboxylic acids and esters and amides thereof, higher-boilingketones and ethers. Examples of these are benzene, toluene, xylene,dimethylformamide, dimethylacetamide, acetic acid, ethyl acetate,diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran,dioxan or 2-butanone.

Suitable catalysts, especially when a non-protic solvent is used, are:p-toluenesulphonic acid, benzoic acid, 4-dimethylaminopyridine,sulphuric acid, hydrochloric acid or naphthalenesulphonic acid. Reactionprocedures of the type mentioned above are customarily used whenpreparing carboxylic acid derivatives. They correspond to generallycustomary laboratory practice.

The anhydrides of the formula II are known or can be prepared byprocesses analogous to known processes.

The aniline derivatives of the formula III are novel and were developedand prepared specifically for the synthesis of the compounds of theformula I. The present invention therefore also relates to them.

The compounds of the formula III are prepared by arranging in anappropriate sequence reaction steps that are known per se, such asetherification of a phenolic hydroxy function, nitration of a phenylnucleus and reduction of the aromatic nitro group to form an aromaticamino group.

The reactions shown in the accompanying schemes 1 to 9 serve toillustrate such methods of preparing the novel compounds of the formulaIII. The substituents R¹ to R⁸ are as defined under formula I. ##STR8##

Although the synthesis of the compounds of the formula I from ananhydride of the formula II and an aniline of the formula III which isoutlined above can be carried out in all cases, it may be wise from thepoint of view of economy or process technology to convert certaincompounds of the formula I into other derivatives of the formula I.Suitable processes for such conversions are those that are known to aperson skilled in the art, such as, for example, oxidation, reduction,esterification, hydrolysis or amidation. A few examples of suchconversions of certain active ingredients of the formula I into otheractive ingredients of the formula I are listed in the following schemes10 to 12. ##STR9##

The acid chlorides of the formula X in which R¹ represents hydrogen orfluorine, R² represents chlorine or bromine, Y represents C₁ -C₈ -alkyl,and Z represents hydrogen or C₁ -C₈ -alkyl are important intermediatesin the preparation of imides of the formula I. This invention relatesalso to them and to their preparation. ##STR10##

The active ingredients of the formula I according to the invention arestable compounds which do not require any particular precautions withregard to their handling.

If the succinimide compounds of the formula I are not synthesiseddirectly from succinimides and phenyl compounds, they may be obtainedalso from the corresponding maleic derivatives. The conversion of themaleic acid imides into the corresponding succinimides is mostadvantageously effected by hydrogenating by means of hydrogen in thepresence of a noble metal catalyst, such as, for example, platinumoxide. The hydrogenation can be carried out under normal pressure.

Depending on the position of the substituents Y and Z, the compounds ofthe formula I may occur in their E- or Z-form, i.e. the succinimides intheir optical isomers and the maleinimides in their geometrical isomers.The radicals R³, R⁴, R⁷ and R⁸ may also contain asymmetric carbon atomsand compounds of the formula I containing such radicals may in turn beresolved into optically active isomers and/or be synthesized as such.This invention relates also to the stereoisomer compounds of the formulaI.

The compounds of the formula I are highly active agrochemical activeingredients that, at suitable rates of application, are outstandinglysuitable as selective herbicides for controlling weeds in crops ofuseful plants. That is to say, at those rates of application, the activeingredients of the formula I are distinguished by good selectiveherbicidal properties towards weeds. Crop plants such as rye, barley,oats, wheat, maize, millet, rice, cotton and soybeans remain virtuallyundamaged at low rates of application. When the rates of application areincreased, the crop plants are only negligibly affected in their growth.If very high rates of application are used, the substances of theformula I exhibit total herbicidal properties.

The selective herbicidal action of the compounds according to theinvention can be observed both when used pre-emergence and when usedpost-emergence. These active ingredients can therefore be used withequally good results both according to the pre-emergence method andaccording to the post-emergence method for selective weed control.

The invention relates also to herbicidal compositions that contain anovel active ingredient of the formula I, and to methods of controllingweeds pre-emergence and post-emergence.

The compounds of the formula I are used in unmodified form or,preferably, in the form of compositions together with the adjuvantsconventionally employed in the art of formulation, and are thereforeformulated in known manner into emulsifiable concentrates, directlysprayable or dilutable solutions, dilute emulsions, wettable powders,soluble powders, dusts, granulates, and also encapsulations in, forexample, polymeric substances. As with the nature of the compositions,the methods of application, such as spraying, atomizing, dusting,scattering or pouring are chosen in accordance with the intendedobjectives and prevailing circumstances.

The formulations, i.e. the agents, preparations or compositionscontaining the active ingredient of the formula I and, whereappropriate, a solid or liquid adjuvant, are prepared in known manner,for example by homogeneously mixing and/or grinding the activeingredients with extenders, such as, for example, solvents, solidcarriers and, where appropriate, surface-active compounds (surfactants).

Suitable solvents are: aromatic hydrocarbons, preferably the fractionsC₈ to C₁₂, such as, for example, xylene mixtures or substitutednaphthalenes, phthalic acid esters such as dibutyl or dioctyl phthalate,aliphatic hydrocarbons such as cyclohexane or paraffins, alcohols andglycols and ethers and esters thereof, such as ethanol, ethylene glycol,ethylene glycol monomethyl or monoethyl ether, ketones such ascyclohexanone, strongly polar solvents such as N-methyl-2-pyrrolidone,dimethyl sulphoxide or dimethylformamide, and also vegetable oils whichmay be epoxidised, such as epoxidised coconut oil or soybean oil; orwater.

The solid carriers used, for example for dusts and dispersible powders,are normally powdered natural minerals, such as calcite, talcum, kaolin,montmorillonite or attapulgite. In order to improve the physicalproperties it is also possible to add highly dispersed silicic acid orhighly dispersed absorbent polymers. Suitable granulated adsorptivecarriers are porous types such as, for example, pumice, broken brick,sepiolite or bentonite; and suitable non-sorbent carriers are, forexample, calcite or sand. In addition, a great number of pre-granulatedmaterials of inorganic or organic nature can be used, such as,especially, dolomite or pulverised plant residues.

Depending on the nature of the active ingredient of the formula I thatis to be formulated, suitable surface-active compounds are non-ionic,cationic and/or anionic surfactants having good emulsifying, dispersingand wetting properties. The term "surfactants" will also be understoodas comprising mixtures of surfactants.

Suitable anionic surfactants can be both so-called water-soluble soapsand water-soluble synthetic surface-active compounds.

Soaps that may be mentioned are the alkali metal salts, alkaline earthmetal salts or unsubstituted or substituted ammonium salts of higherfatty acids (C₁₀ -C₂₂), such as, for example, the sodium or potassiumsalts of oleic or stearic acid, or of natural fatty acid mixtures whichcan be obtained, for example, from coconut oil or tallow oil. Mentionmay also be made of fatty acid methyltaurin salts.

More frequently, however, so-called synthetic surfactants are used,especially fatty sulphonates, fatty sulphates, sulphonated benzimidazolederivatives or alkylarylsulphonates.

The fatty sulphonates or sulphates are, as a rule, in the form of alkalimetal salts, alkaline earth metal salts or unsubstituted or substitutedammonium salts and contain an alkyl radical having from 8 to 22 carbonatoms, alkyl also including the alkyl moiety of acyl radicals, forexample the sodium or calcium salt of lignosulphonic acid, ofdodecylsulphate or of a mixture of fatty alcohol sulphates prepared fromnatural fatty acids.

These compounds also include the salts of sulphuric acid esters andsulphonic acids of fatty alcohol/ethylene oxide adducts. The sulphonatedbenzimidazole derivatives preferably contain 2 sulphonic acid groups andone fatty acid radical containing from 8 to 22 carbon atoms. Examples ofalkylarylsulphonates are the sodium, calcium or triethanolamine salts ofdodecylbenzenesulphonic acid, of dibutylnaphthalenesulphonic acid or ofa naphthalenesulphonic acid/formaldehyde condensation product.

Also suitable are corresponding phosphates, such as, for example, saltsof the phosphoric acid ester of an adduct of p-nonylphenol with from 4to 14 moles of ethylene oxide, or phospholipids.

Non-ionic surfactants are especially polyglycol ether derivatives ofaliphatic or cycloaliphatic alcohols, of saturated or unsaturated fattyacids and alkylphenols, which derivatives may contain from 3 to 10glycol ether groups and from 8 to 20 carbon atoms in the (aliphatic)hydrocarbon moiety and from 6 to 18 carbon atoms in the alkyl moiety ofthe alkylphenols.

Further suitable non-ionic surfactants are the water-soluble adducts ofpolyethylene oxide with polypropylene glycol, ethylenediaminepolypropylene glycol and alkylpolypropylene glycol containing from 1 to10 carbon atoms in the alkyl chain, which adducts contain from 20 to 250ethylene glycol ether groups and from 10 to 100 propylene glycol ethergroups. The compounds mentioned usually contain from 1 to 5 ethyleneglycol units per propylene glycol unit.

Examples of non-ionic surfactants that may be mentioned arenonylphenolpolyethoxyethanols, castor oil polyglycol ethers,polypropylene/polyethylene oxide adducts,tributylphenoxypolyethoxyethanol, polyethylene glycol andoctylphenoxypolyethoxyethanol.

Fatty acid esters of polyoxyethylene sorbitan such as polyoxyethylenesorbitan trioleate are also suitable.

Cationic surfactants are especially quaternary ammonium salts thatcontain, as N-substituent, at least one alkyl radical having from 8 to22 carbon atoms and, as further substituents, lower optionallyhalogenated alkyl, benzyl or lower hydroxyalkyl radicals. The salts arepreferably in the form of halides, methyl sulphates or ethyl sulphates,for example stearyltrimethylammonium chloride orbenzyldi(2-chloroethyl)ethylammonium bromide.

The surfactants customarily employed in the art of formulation aredescribed, inter alia, in the following publications:

"McCutcheon's Detergent and Emulsifiers Annual" Publishing Corp.,Ridgewood, N.J., 1981;

H. Stache, "Tensid-Taschenbuch", 2nd edition, C. Hanser Verlag, Munich,Vienna, 1981;

M. and J. Ash, "Encyclopedia of Surfactants", Vol. I-III, ChemicalPublishing Co., New York, 1980-1981.

The herbicidal preparations usually contain from 0.1 to 95%, especiallyfrom 0.1 to 80%, active ingredient of the formula I, from 1 to 99.9% ofa solid or liquid adjuvant and from 0 to 25%, especially from 0.1 to25%, of a surfactant.

Preferred formulations have especially the following compositions(%=percent by weight):

    ______________________________________                                        Emulsifiable concentrates:                                                    active ingredient:                                                                           1 to 20%, preferably 5 to 10%                                  surfactants:   5 to 30%, preferably 10 to 20%                                 liquid carriers:                                                                             50 to 94%, preferably 70 to 85%                                Dusts:                                                                        active ingredient:                                                                           0.1 to 10%, preferably 0.1 to 1%                               solid carrier: 99.9 to 90%, preferably 99.9 to 99%                            Suspension concentrates:                                                      active ingredient:                                                                           5 to 75%, preferably 10 to 50%                                 water:         94 to 25%, preferably 88 to 30%                                surfactant:    1 to 40%, preferably 2 to 30%                                  Wettable powder:                                                              active ingredient:                                                                           0.5 to 90%, preferably 1 to 80%                                surfactant:    0.5 to 20%, preferably 1 to 15%                                solid carrier: 5 to 95%, preferably 15 to 90%                                 Granulates:                                                                   active ingredient:                                                                           0.5 to 30%, preferably 3 to 15%                                solid carrier: 99.5 to 70%, preferably 97 to 85%                              ______________________________________                                    

Whereas concentrates are preferred as commercial products, the end userwill as a rule use dilute formulations. The formulations can be dilutedto a concentration as low as 0.001% active ingredient. The rates ofapplication are normally from 0.001 to 4 kg active ingredient/ha,preferably from 0.005 to 1 kg active ingredient/ha.

The compositions may also contains further additives such asstabilisers, antifoams, viscosity regulators, binders, tackifiers andalso fertilisers or other active ingredients for achieving specialeffects.

The following Examples illustrate the preparation of the imides of theformula I. Temperatures are given in degrees Celsius.

EXAMPLE 1 Preparation of N-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleicacid imide (intermediate) ##STR11##

A mixture of 46.5 g of 3-amino-4-fluorobenzoic acid and 37.8 g ofdimethylmaleic anhydride in 200 ml of glacial acetic acid is stirred for12 hours at an oil bath temperature of 130°-40°. After cooling, themixture is poured onto ice-water, and the resulting precipitate isfiltered with suction, washed with water and dried. Recrystallisationfrom ethanol/water yields 70.3 g ofN-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide which meltsat 238°-240°.

EXAMPLE 2 Preparation ofN-(2-fluoro-4-nitro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide(intermediate) ##STR12##

26.3 g of N-(2-fluoro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide areintroduced in portions, at 5°, into 230 ml of 96% sulphuric acid. Thereis then added dropwise to this mixture, while stirring vigorously at thesame temperature, 5 ml of 100% nitric acid. The whole is further stirredovernight at room temperature and then poured into ice. The productwhich precipitates is filtered with suction, washed with water, driedand recrystallised from acetonitrile. 28 g ofN-(2-fluoro-5-carboxy-4-nitrophenyl)-2,3-dimethylmaleic acid imide whichhas a melting point of 264°-265° is thus obtained.

EXAMPLE 3 Preparation ofN-(2-fluoro-4-amino-5-carboxyphenyl)-2,3-dimethylmaleic acid imide(intermediate) ##STR13##

67.8 g of N-(2-fluoro-5-carboxy-4-nitrophenyl)-2,3-dimethylmaleic acidimide are hydrogenated using hydrogen in the presence of 14 g of Raneynickel catalyst in 1000 ml of tetrahydrofuran at a temperature of20°-25° under normal pressure. When the stoichiometric amount ofhydrogen has been consumed, the catalyst is separated off and thesolution is concentrated by evaporation. 56.7 g ofN-(2-fluoro-5-carboxy-4-aminophenyl)-2,3-dimethylmaleic acid imidehaving a melting point of 270° are thus obtained.

EXAMPLE 4 Preparation ofN-(2-fluoro-4-chloro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide##STR14##

11.4 g of N-(2-fluoro-5-carboxy-4-aminophenyl)-2,3-dimethylmaleic acidimide are introduced in portions, at a temperature of 25°-30°, into 60ml of glacial acetic acid and 60 ml of 96% sulphuric acid and the wholeis stirred at that temperature for 1 hour. The solution is then stirredat 5° and an aqueous solution of 2.9 g of sodium nitrite in 17 ml ofwater is added dropwise thereto. The resulting diazo solution is addedin portions, while stirring vigorously at 30°, to a solution of 4.5 g ofcopper(I) chloride in 32 ml of concentrated hydrochloric acid. When theevolution of nitrogen has ceased, the reaction mixture is heated at 60°for a further 30 minutes, while stirring, and then poured onto ice. Theproduct which precipitates is filtered with suction, washed with waterand recrystallised from methanol/water. 9.8 g ofN-(2-fluoro-5-carboxy-4-chlorophenyl)-2,3-dimethylmaleic acid imidehaving a melting point of 230°-231° are obtained.

EXAMPLE 5 Preparation ofN-(2-fluoro-4-chloro-5-chlorocarbonylphenyl)-2,3-dimethylmaleic acidimide (intermediate) ##STR15##

A mixture of 6 g ofN-(2-fluoro-5-carboxy-4-chlorophenyl)-2,3-dimethylmaleic acid imide, 0.5ml of dimethylmaleinimide, 2 ml of thionyl chloride and 50 ml of tolueneis heated under reflux for 4 hours. After cooling, the whole isconcentrated by evaporation in vacuo. 6 g ofN-(2-fluoro-5-chlorocarbonyl-4-chlorophenyl)-2,3-dimethylmaleic acidimide having a melting point of 123°-124° are obtained.

EXAMPLE 6 Preparation ofN-(2-fluoro-4-chloro-5-isopropoxycarbonylphenyl)-2,3-dimethylmaleic acidimide ##STR16##

6 g of N-(2-fluoro-5-chlorocarbonyl-4-chlorophenyl)-2,3-dimethylmaleicacid imide are added dropwise, while stirring at room temperature, to amixture of 4 ml of isopropanol, 4 ml of triethylamine and 100 ml oftoluene. After a reaction time of 6 hours, the triethylaminehydrochloride is separated off by filtration and the filtrate isconcentrated by evaporation. By recrystallising the residue fromethanol/water, 4.2 g ofN-(2-fluoro-4-chloro-5-isopropoxycarbonylphenyl)-2,3-dimethylmaleic acidimide having a melting point of 161°-162° are obtained.

EXAMPLE 7 Preparation ofN-[2-fluoro-4-chloro-5-(3-chlorallyloxycarbonyl)-phenyl]-2,3-maleic acidimide ##STR17##

A mixture of 3 g ofN-(2-fluoro-4-chloro-5-carboxyphenyl)-2,3-dimethylmaleic acid imide, 4.5g of potassium carbonate, 1 ml of 1,3-dichloropropene and 50 ml of2-butanone is heated under reflux for 16 hours. The precipitate isseparated off and the filtrate is concentrated by evaporation. 3.3 g ofN-[2-fluoro-5-(3-chlorallyloxycarbonyl)-4-chlorophenyl]-2,3-dimethylmaleicacid imide are obtained in the form of an oil. Refractive index n_(D) ²⁴1.5640.

EXAMPLE 8 Preparation ofN-(2-fluoro-5-methylcarbonylphenyl)-2,3-dimethylmaleic acid imide(intermediate) ##STR18##

A mixture of 3 g of 5-amino-4-fluoroacetophenone, 2.5 g ofdimethylmaleic anhydride and 50 ml of glacial acetic acid is heatedunder reflux overnight. The reaction mixture is then poured onto ice,and the resulting precipitate is filtered with suction, washed withwater and dried. 2.3 g ofN-(2-fluoro-5-methylcarbonylphenyl)-2,3-dimethylmaleic acid imide havinga melting point of 130°-131° are thus obtained. By nitration, reductionand reaction with sodium nitrite and copper(I) chloride in accordancewith Examples 2, 3 and 4 there can be obtained from this compoundN-(2-fluoro-4-chloro-5-methylcarbonyl)-2,3-dimethylmaleic acid imide,m.p. 95°-97°.

EXAMPLE 9 Preparation of N-(2-fluoro-4-chlorophenyl)-2,3-dimethylmaleicacid imide ##STR19##

A mixture of 126 g (1.0 mol) of dimethylmaleic anhydride, 145.5 g (1.0mol) of 2-fluoro-4-chloroaniline and 2 g of 4-dimethylaminopyridine isheated under reflux in 800 ml of o-xylene for 16 hours using a waterseparator. The whole is then evaporated to dryness in vacuo and theresidue is dissolved in a 1:1 mixture of ethyl acetate:ether and washedwith each of 1N hydrochloric acid, 1N sodium hydroxide solution andwater. Afer drying over sodium sulphate and evaporating off the solvent,the residue (227.5 g) is recrystallised from methanol. In this mannerthere are obtained 211.1 g (84% of the theoretical yield) of the titleproduct in the form of colourless crystals which melt at 96°-97°.

EXAMPLE 10 Preparation ofN-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2,3-dimethylmaleic acid imide##STR20##

A mixture of 20.4 g (0.1 mol) of 2-fluoro-4-chloro-5-isopropoxyanilineand 12.6 g (0.1 mol) of dimethylmaleic anhydride in 100 ml of glacialacetic acid is stirred for 6 hours at a temperature of 130°-140°. It isthen allowed to cool to room temperature and the almost black reactionsolution is concentrated in a rotary evaporator. The residue is taken upin ethyl acetate and the solution is washed in succession with water, 1Msoda solution, water and concentrated salt brine. It is then dried oversodium sulphate, filtered and concentrated in vacuo. The dark oilremaining is crystallised from ethanol with the aid of activated carbon.17.6 g of title product (56.5% of the theoretical yield) which melts at93°-95° is thus obtained.

EXAMPLE 11 Preparation ofN-(2-fluoro-4-chlorophenyl)-2,3-dimethylsuccinimide ##STR21##

A mixture of 7.5 g (0.03 mol) ofN-(4-chloro-2-fluorophenyl)-2,3-dimethylmaleic acid imide and 400 mg ofplatinum oxide (PtO₂) is hydrogenated with hydrogen in 75 ml of ethylacetate at room temperature under normal pressure. After about 5 hours,the reduction is complete. The catalyst is then filtered off and thefiltrate is concentrated in vacuo. 7.6 g (99% of the theoretical yield)of cis-N-(2-fluoro-4-chlorophenyl)-2,3-dimethylsuccinimide in the formof a yellowish oil which is uniform in a thin-layer chromatogram remainas residue.

¹ H-NMR (300 MH₂, CDCl₃) 1.34 (d, 2xCH₃); 3.12 (m, CH--CH); 7.2 (m, 3Ar. H).

EXAMPLE 12 Preparation ofN-(2-fluoro-4-chloro-5-isopropoxyphenyl)-2,3-dimethyl-succinimide##STR22##

A mixture of 9.4 g (0.03 mol) ofN-(2-fluoro-4-chloro-5-isopropoxyphenyl)-2,3-dimethylmaleic acid imideand 500 mg of platinum oxide (PtO₂) in 100 ml of ethyl acetate ishydrogenated with hydrogen at room temperature under normal pressure.After about 5 hours, when the absorption of hydrogen has ceased, thecatalyst is filtered off and the filtrate is concentrated to dryness.7.9 g (85% of the theoretical yield) of an almost colourless oil whichis uniform in a thin-layer chromatogram are obtained as residue andcrystallised from isopropyl ether. Thecis-N-(2-fluoro-4-chloro-5-isopropoxyphenyl)-2,3-dimethyl-succinimide soobtained has a melting point of 101°-102°.

EXAMPLE 13 Preparation ofN-(2-fluoro-4-chloro-5-isopropoxyphenyl)-2-ethyl-3-methylmaleic acidimide ##STR23##

5 g of 2-ethyl-3-methylmaleic anhydride, 7.3 g of2-fluoro-4-chloro-5-isopropoxyaniline and 0.61 g of4-dimethylaminopyridine are combined in 100 ml of xylene in adistillation apparatus and the solvent is slowly distilled off. After 5hours, the reaction is complete. The xylene still present is removedunder a water-jet vacuum. The dark residue is taken up in ethyl acetateand extracted with 2M hydrochloric acid, water, 10% sodium bicarbonatesolution and lastly with saturated sodium chloride solution. Afterdrying over sodium sulphate, the ethyl acetate is distilled off in arotary evaporator and the residue is chromatographed over a column ofsilica gel with hexane:ethyl acetate 1:1. After evaporating the solvent,5 g of the title compound are obtained in the form of a red oil having arefractive index of n_(D) ²² =1.5351.

EXAMPLE 14 Preparation ofN-(2-fluoro-4-chloro-5-hydroxyphenyl)-2,3-dimethylmaleic acid imide##STR24##

A mixture of 16.1 g of 2-fluoro-4-chloro-5-hydroxyaniline and 12.6 g ofdimethylmaleic acid anhydride in 100 ml of propionic acid are heated to150° and stirred for 12 hours at that temperature. The reaction mixtureis then allowed to cool and concentrated. The residue is cristallizedfrom methanol and yields 27.3 g ofN-(2-fluoro-4-chloro-5-hydroxyphenyl)-2,3-dimethylmaleic acid imidemelting at 170°-171°.

EXAMPLE 15 Preparation ofN-(2-fluoro-4-chloro-5-propynyloxyphenyl)-2,3-dimethylmaleic acid imide.##STR25##

A mixture of 5.4 g ofN-(2-fluoro-4-chloro-5-hydroxyphenyl)-2,3-dimethyl-maleic acid imide,2.4 g of propynylbromide and 4 g of potassium carbonate in 100 ml ofbutan-2-on are heated to 100° and stirred for 2 hours at thattemperature. The reaction mixture is then allowed to cool down, theprecipitation is filtered off, and the filtrate is concentrated todryness. After recrystallisation of the residue, 4.5 g ofN-(2-fluoro-4-chloro-5-propynyloxyphenyl)2,3-dimethylmaleic acidanhydride is obtained, which melt at 149°-150°.

The compounds listed in the following Tables are prepared in a manneranalogous to these Examples.

                  TABLE 1                                                         ______________________________________                                         ##STR26##                                                                    No.  R.sup.1                                                                             R.sup.2                                                                             A                                                            ______________________________________                                        1.01 F     Cl    COCH.sub.3                                                   1.02 F     Cl    COCH.sub.2 Cl                                                1.03 F     Cl    COCF.sub.3                                                   1.04 F           COCH.sub.3                                                   1.05 F     Cl    C(CH.sub.3)NOH                                               1.06 F     Cl    C(CH.sub.3)NOCH.sub.3                                        1.07 F     Cl    C(CN)NOH                                                     1.08 F     Br    C(CN)NOC.sub.2 H.sub.5                                       1.09 F     Cl    C(CN)NOCH(CH.sub.3)COOCH.sub.3                               1.10 F     Cl                                                                                   ##STR27##                                                   1.11 F     Cl                                                                                   ##STR28##                                                   1.12 F     Cl                                                                                   ##STR29##                                                   1.13 F     Cl    COOH               m.p. 230-231°                      1.14 F     Br    COOH               m.p. 231-233°                      1.15 F     Cl    COOCH.sub.3        m.p. 137-138°                      1.16 F     Cl    COOCH(CH.sub.3).sub.2                                                                            m.p. 101-102°                      1.17 H     Cl    COOH                                                         1.18 H     Cl    COOCH.sub.3                                                  1.19 H     Cl    COOCH(CH.sub.3).sub.2                                        1.20 F     Cl    COSCH.sub.2 COOCH.sub.3                                                                          m.p. 78-81°                        1.21 F     Cl    COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                     1.22 F     Cl    COSCH(CH.sub.3)COOCH.sub.3                                                                       n.sub.D.sup.23 = 1.5668                   1.23 F     Cl    COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                        1.24 F     Cl    OH                 m.p. 170-171°                      1.25 F     Br    OH                                                           1.26 F     Cl    OCH.sub.3                                                    1.27 F     Cl    OCH(CH.sub.3).sub.2                                                                              m.p. 95-97°                        1.28 F     Br    OCH.sub.2 CHCH.sub.2                                         1.29 F     Cl    OCH.sub.2 CHCHCl                                             1.30 F     Cl    OCH.sub.2 CClCH.sub.2                                        1.31 F     Cl    OCH.sub.2 COOCH.sub.3                                        1.32 F     Cl    OCH.sub.2 COOCH(CH.sub.3).sub. 2                             1.33 F     Cl    SH                                                           1.34 F     Br    SH                                                           1.35 F     Cl    SCH.sub.3                                                    1.36 F     Cl    SCH(CH.sub.3).sub.2                                          1.37 F     Cl    SCH.sub.2 CHCHCl                                             1.38 F     Cl    SCH.sub.2 COOH     m.p. 165-167°                      1.39 F     Br    SCH.sub.2 COOH                                               1.40 F     Cl    SCH(CH.sub.3)COOH                                            1.41 F     Cl    SCH.sub.2 COOCH.sub.3                                        1.42 F     Cl    SCH(CH.sub.3)COOCH.sub.3                                     1.43 F     Cl    OCClCHCl           m.p. 127-130°                      1.44 F     Cl    OCF.sub.3          m.p. 79-82°                        1.45 F     Cl    OCClF.sub.2        m.p. 90-93°                        1.46 F     H     COOH               m.p. 238-240°                      1.47 H     Br    COOCH(CH.sub.3).sub.2                                                                            m.p. 93-95°                        1.48 F     Br    COOOCH(CH.sub.3).sub.2                                                                           m.p. 104-105°                      1.49 F     Br    COSCH(CH.sub.3)COOCH.sub.3                                                                       m.p. 82-83°                        1.50 F     Cl    COSCH(CH.sub.3)COOC.sub.2 H.sub.5                                                                n.sub.D.sup.23 = 1.5529                   1.51 F     Cl    COOCH.sub.2 CH(CH.sub.3).sub.2                                                                   m.p. 83-84°                        1.52 F     Cl    COOC.sub.2 H.sub.5 m.p. 101-102°                      1.53 F     Cl    COOCH(CH.sub.3)COOCH.sub.3                                                                       n.sub.D.sup.23 = 1.5243                   1.54 F     Br    COOCH(CH.sub.3)COOCH.sub.3                                                                       n.sub.D.sup.23 = 1.5398                   1.55 F     Br    COOCH(CH.sub.3)CH.sub.2 SC.sub.2 H.sub.5                                                         n.sub.D.sup.23 = 1,5301                   1.56 F     Br    COOCH(CH.sub.3)CH.sub.2 SCH.sub.3                                                                n.sub.D.sup.23 = 1,5670                   1.57 F     Br    COOCH(CH.sub.3)CH.sub.2 SCH(CH.sub.3).sub.2                                                      n.sub.D.sup.23 = 1,5271                   1.58 F     Br    COSCH(CH.sub.3)COOC.sub.2 H.sub.5                                                                n.sub.D.sup.23 = 1,5530                   1.59 F     Br    COSCH(CH.sub.3)COOCH(CH.sub.3).sub.2                                                             n.sub.D.sup.23 = 1,5252                   1.60 F     Cl    COOCH(CH.sub.3)CH.sub.2 SC.sub.2 H.sub.5                                                         n.sub.D.sup.23 = 1,5489                   1.61 F     Cl    COOCH.sub.2 CHCHCl n.sub.D.sup.24 = 1,5640                   1.62 F     Cl    COOCH(CH.sub.3)COOC.sub.2 H.sub.5                                                                n.sub.D.sup.24 = 1,5319                   1.63 F     Cl    COOCH(CH.sub.3)CH.sub.2 SC(CH.sub.3).sub.3                                                       n.sub.D.sup.23 = 1,5373                   1.64 F     Cl    COSCH(CH.sub.3)COOCH(CH.sub.3).sub.2                                                             n.sub.D.sup.23 = 1,5389                   1.65 F     Cl    COOCH.sub.2 CHCH.sub.2                                                                           n.sub.D.sup.25 = 1,5532                   1.66 F     Cl    COSCH.sub.2 COOC.sub.2 H.sub.5                                                                   n.sub.D.sup.23 = 1,5639                   1.67 F     Cl    COOCH(CH.sub.3)CH.sub.2 SCH.sub.3 H.sub.7n                                                       n.sub.D.sup.25 = 1,5425                   1.68 F     Cl    COOCH(CH.sub.3)CH.sub.2 SCH(CH.sub.3).sub.2                                                      n.sub.D.sup.24 = 1,5432                   1.69 F     Cl    COOCH(C.sub.3)CH.sub.2 SC.sub.4 H.sub.9n                                                         n.sub.D.sup.25 = 1,5309                   1.70 F     H     COCH.sub.3         Smp.                                                                          130-131°                           1.71 F     Cl    COOCH(CH.sub.3)CH.sub.2 SCH.sub.3                                                                n.sub.D.sup.25 = 1,5406                   1.72 F     Cl    OCH.sub.2 CCH      Smp.                                                                          149-150°                           1.73 F     Cl    OCH(CH.sub.3)COOCH.sub.3                                                                         Smp.                                                                          117-118°                           1.74 F     Cl                                                                                   ##STR30##         n.sub.D.sup.25 = 1,5422                   1.75 F     Cl                                                                                   ##STR31##                                                   1.76 F     Cl    COOCH.sub.2CHCClCH.sub.3                                     1.77 F     Cl                                                                                   ##STR32##                                                   1.78 F     Cl    COOCH.sub.2C CH                                              1.79 F     Br    COOCH.sub.2CHCCl.CH.sub.3                                    1.80 F     Br    COOCH.sub.2CClCH.sub.2                                       1.81 F     Br    COOCH.sub.2CHCHCl                                            1.82 F     Br    COOCH.sub.2CBrCH.sub.2                                       1.83 F     Br    OCH.sub.2CCH                                                 1.84 F     Cl    OCH(CH.sub.3)CH.sub.2SCH.sub.3                                                                   n.sub.D.sup.23 = 1,5468                   ______________________________________                                    

                  TABLE 2                                                         ______________________________________                                         ##STR33##                                                                    No.   R.sup.1                                                                             R.sup.2                                                                              A                                                          ______________________________________                                        2.01  F     Cl     COCH.sub.3                                                 2.02  F     Cl     COCH.sub.2 Cl                                              2.03  F     Cl     COCF.sub.3                                                 2.04  F            COCH.sub.3                                                 2.05  F     Cl     C(CH.sub.3)NOH                                             2.06  F     Cl     C(CH.sub.3)NOCH.sub.3                                      2.07  F     Cl     C(CN)NOH                                                   2.08  F     Br     C(CN)NOC.sub.2 H.sub.5                                     2.09  F     Cl     C(CN)NOCH(CH.sub.3)COOCH.sub.3                             2.10  F     Cl                                                                                    ##STR34##                                                 2.11  F     Cl                                                                                    ##STR35##                                                 2.12  F     Cl                                                                                    ##STR36##                                                 2.13  F     Cl     COOH                                                       2.14  F     Br     COOH                                                       2.15  F     Cl     COOCH.sub.3                                                2.16  F     Cl     COOCH(CH.sub.3).sub.2                                      2.17  H     Cl     COOH                                                       2.18  H     Cl     COOCH.sub.3                                                2.19  H     Cl     COOCH(CH.sub.3).sub.2                                      2.20  F     Cl     COSCH.sub.2 COOCH.sub.3                                    2.21  F     Cl     COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                   2.22  F     Cl     COSCH.sub.2 (CH.sub.3)COOCH.sub.3                          2.23  F     Cl     COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                      2.24  F     Cl     OH                                                         2.25  F     Br     OH                                                         2.26  F     Cl     OCH.sub.3                                                  2.27  F     Cl     OCH(CH.sub.3).sub.2                                                                              m.p. 102°                        2.28  F     Br     OCH.sub.2 CHCH.sub.2                                       2.29  F     Cl     OCH.sub.2 CHCHCl                                           2.30  F     Cl     OCH.sub.2 CClCH.sub.2                                      2.31  F     Cl     OCH.sub.2 COOCH.sub.3                                      2.32  F     Cl     OCH.sub.2 COOCH(CH.sub.3).sub.2                            2.33  F     Cl     SH                                                         2.34  F     Br     SH                                                         2.35  F     Cl     SCH.sub.3                                                  2.36  F     Cl     SCH(CH.sub.3).sub.2                                        2.37  F     Cl     SCH.sub.2 CHCHCl                                           2.38  F     Cl     SCH.sub.2 COOH                                             2.39  F     Br     SCH.sub.2 COOH                                             2.40  F     Cl     SCH(CH.sub.3)COOH                                          2.41  F     Cl     SCH.sub.2 COOCH.sub.3                                      2.42  F     Cl     SCH(CH.sub.3)COOCH.sub.3                                   2.43  F     Cl     H                  oil                                     2.44  F     Cl     OCH.sub.2 CCH                                              2.45  F     Cl     OCH(CH.sub.3)COOCH.sub.3                                   ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                         ##STR37##                                                                    No.  R.sup.1                                                                             R.sup.2                                                                             A                                                            ______________________________________                                        3.01 F     Cl    COCH.sub.3                                                   3.02 F     Cl    COCH.sub.2 Cl                                                3.03 F     Cl    COCF.sub.3                                                   3.04 F           COCH.sub.3                                                   3.05 F     Cl    C(CH.sub.3)NOH                                               3.06 F     Cl    C(CH.sub.3)NOCH.sub.3                                        3.07 F     Cl    C(CN)NOH                                                     3.08 F     Br    C(CN)NOC.sub.2 H.sub.5                                       3.09 F     Cl    C(CN)NOCH(CH.sub.3)COOCH.sub.3                               3.10 F     Cl                                                                                   ##STR38##                                                   3.11 F     Cl                                                                                   ##STR39##                                                   3.12 F     Cl                                                                                   ##STR40##                                                   3.13 F     Cl    COOH               m.p. 165°                          3.14 F     Br    COOH                                                         3.15 F     Cl    COOCH.sub.3                                                  3.16 F     Cl    COOCH(CH.sub.3).sub.2                                                                            m.p. 68-69°                        3.17 H     Cl    COOH                                                         3.18 H     Cl    COOCH.sub.3                                                  3.19 H     Cl    COOCH(CH.sub.3).sub.2                                                                            n.sub.D.sup.22 = 1.5458                   3.20 F     Cl    COSCH.sub.2 COOCH.sub.3                                      3.21 F     Cl    COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                     3.22 F     Cl    COSCH.sub.2 (CH.sub.3)COOCH.sub.3                            3.23 F     Cl    COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                        3.24 F     Cl    OH                 m.p. 74-75°                        3.25 F     Br    OH                                                           3.26 F     Cl    OCH.sub.3                                                    3.27 F     Cl    OCH(CH.sub.3).sub.2                                                                              n.sub.D.sup.22 = 1,5351                   3.28 F     Br    OCH.sub.2 CHCH.sub.2                                         3.29 F     Cl    OCH.sub.2 CHCHCl   n.sub.D.sup.23 = 1,5572                   3.30 F     Cl    OCH.sub.2 CClCH.sub.2                                        3.31 F     Cl    OCH.sub.2 COOCH.sub.3                                        3.32 F     Cl    OCH.sub.2 COOCH(CH.sub.3 ).sub.2                             3.33 F     Cl    SH                                                           3.34 F     Br    SH                                                           3.35 F     Cl    SCH.sub.3                                                    3.36 F     Cl    SCH(CH.sub.3).sub.2                                          3.37 F     Cl    SCH.sub.2 CHCHCl                                             3.38 F     Cl    SCH.sub.2 COOH                                               3.39 F     Br    SCH.sub.2 COOH                                               3.40 F     Cl    SCH(CH.sub.3)COOH                                            3.41 F     Cl    SCH.sub.2 COOCH.sub.3                                        3.42 F     Cl    SCH(CH.sub.3)COOCH.sub.3                                     3.43 F     Cl    OCH.sub.2 CCH      m.p. 98-99°                        3.44 F     Cl    OCH(CH.sub.3)COOCH.sub.3                                                                         n.sub.D.sup.24 = 1,5308                   3.45 F     Cl    COOCH(CH.sub.3)CH.sub.2SCH.sub.3                             3.46 F     Cl    COOCH(CH.sub.3)CH.sub.2SC.sub.2 H.sub.5                      3.47 F     Cl    COOCH.sub.2CClCH.sub.2                                       3.48 F     Cl    COOCH.sub.2CHCHCl                                            3.49 F     Cl    COOCH.sub.2CHCClCH.sub.3                                     3.50 F     Cl    COOCH.sub.2CBrCH.sub.2                                       3.60 F     Cl    COOCH.sub.2CBrCHBr                                           3.61 F     Br    COOCH.sub.2CClCH.sub.2                                       3.62 F     Br    COOCH.sub.2CHCHCl                                            3.63 F     Br    COOCH.sub.2CHCClCH.sub.3                                     3.64 F     Br    COOCH.sub.2CBrCH.sub.2                                       3.65 F     Br    OCH.sub.2CCH                                                 3.66 F     Br                                                                                   ##STR41##                                                   ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                         ##STR42##                                                                    No.     R.sup.1                                                                             R.sup.2 A                                                       ______________________________________                                        4.01    F     Cl      COCH.sub.3                                              4.02    F     Cl      COCH.sub.2 Cl                                           4.03    F     Cl      COCF.sub.3                                              4.04    F             COCH.sub.3                                              4.05    F     Cl      C(CH.sub.3)NOH                                          4.06    F     Cl      C(CH.sub.3)NOCH.sub.3                                   4.07    F     Cl      C(CN)NOH                                                4.08    F     Br      C(CN)NOC.sub.2 H.sub.5                                  4.09    F     Cl      C(CN)NOCH(CH.sub.3)COOCH.sub.3                          4.10    F     Cl                                                                                     ##STR43##                                              4.11    F     Cl                                                                                     ##STR44##                                              4.12    F     Cl                                                                                     ##STR45##                                              4.13    F     Cl      COOH                                                    4.14    F     Br      COOH                                                    4.15    F     Cl      COOCH.sub.3                                             4.16    F     Cl      COOCH(CH.sub.3).sub.2                                   4.17    H     Cl      COOH                                                    4.18    H     Cl      COOCH.sub.3                                             4.19    H     Cl      COOCH(CH.sub.3).sub.2                                   4.20    F     Cl      COSCH.sub.2 COOCH.sub.3                                 4.21    F     Cl      COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                4.22    F     Cl      COSCH.sub.2 (CH.sub.3)COOCH.sub.3                       4.23    F     Cl      COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                   4.24    F     Cl      OH                                                      4.25    F     Br      OH                                                      4.26    F     Cl      OCH.sub.3                                               4.27    F     Cl      OCH(CH.sub.3).sub.2                                     4.28    F     Br      OCH.sub.2 CHCH.sub.2                                    4.29    F     Cl      OCH.sub.2 CHCHCl                                        4.30    F     Cl      OCH.sub.2 CClCH.sub.2                                   4.31    F     Cl      OCH.sub.2 COOCH.sub.3                                   4.32    F     Cl      OCH.sub.2 COOCH(CH.sub.3).sub.2                         4.33    F     Cl      SH                                                      4.34    F     Br      SH                                                      4.35    F     Cl      SCH.sub.3 -4.36 F Cl SCH(CH.sub.3).sub.2                4.37    F     Cl      SCH.sub.2 CHCHCl                                        4.38    F     Cl      SCH.sub.2 COOH                                          4.39    F     Br      SCH.sub.2 COOH                                          4.40    F     Cl      SCH(CH.sub.3)COOH                                       4.41    F     Cl      SCH.sub.2 COOCH.sub.3                                   4.42    F     Cl      SCH(CH.sub.3)COOCH.sub.3                                4.43    F     Cl      OCH.sub.2 CCH                                           4.44    F     Cl      OCH(CH.sub.3)COOCH.sub.3                                ______________________________________                                    

                  TABLE 5                                                         ______________________________________                                         ##STR46##                                                                    No.     R.sup.1                                                                             R.sup.2 A                                                       ______________________________________                                        5.01    F     Cl      COCH.sub.3                                              5.02    F     Cl      COCH.sub.2 Cl                                           5.03    F     Cl      COCF.sub.3                                              5.04    F             COCH.sub.3                                              5.05    F     Cl      C(CH.sub.3)NOH                                          5.06    F     Cl      C(CH.sub.3)NOCH.sub.3                                   5.07    F     Cl      C(CN)NOH                                                5.08    F     Br      C(CN)NOC.sub.2 H.sub.5                                  5.09    F     Cl      C(CN)NOCH(CH.sub.3)COOCH.sub.3                          5.10    F     Cl                                                                                     ##STR47##                                              5.11    F     Cl                                                                                     ##STR48##                                              5.12    F     Cl                                                                                     ##STR49##                                              5.13    F     Cl      COOH                                                    5.14    F     Br      COOH                                                    5.15    F     Cl      COOCH.sub.3                                             5 16    F     Cl      COOCH(CH.sub.3).sub.2                                   5.17    H     Cl      COOH                                                    5.18    H     Cl      COOCH.sub.3                                             5.19    H     Cl      COOCH(CH.sub.3).sub.2                                   5.20    F     Cl      COSCH.sub.2 COOCH.sub.3                                 5.21    F     Cl      COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                5.22    F     Cl      COSCH.sub.2 (CH.sub.3)COOCH.sub.3                       5.23    F     Cl      COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                   5.24    F     Cl      OH                                                      5.25    F     Br      OH                                                      5.26    F     Cl      OCH.sub.3                                               5.27    F     Cl      OCH(CH.sub.3).sub.2 n.sub.D.sup.23 = 1,5298             5.28    F     Br      OCH.sub.2 CHCH.sub.2                                    5.29    F     Cl      OCH.sub.2 CHCHCl                                        5.30    F     Cl      OCH.sub.2 CClCH.sub.2                                   5.31    F     Cl      OCH.sub.2 COOCH.sub.3                                   5.32    F     Cl      OCH.sub.2 COOCH(CH.sub.3).sub.2                         5.33    F     Cl      SH                                                      5.34    F     Br      SH                                                      5.35    F     Cl      SCH.sub.3                                               5.36    F     Cl      SCH(CH.sub.3).sub. 2                                    5.37    F     Cl      SCH.sub.2 CHCHCl                                        5.38    F     Cl      SCH.sub.2 COOH                                          5.39    F     Br      SCH.sub.2 COOH                                          5.40    F     Cl      SCH(CH.sub.3)COOH                                       5.41    F     Cl      SCH.sub.2 COOCH.sub.3                                   5.42    F     Cl      SCH(CH.sub.3)COOCH.sub.3                                5.43    F     Cl      OCH.sub.2 CCH                                           5.44    F     Cl      OCH(CH.sub.3)COOCH.sub.3                                ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                         ##STR50##                                                                    No.     R.sup.1                                                                             R.sup.2 A                                                       ______________________________________                                        6.01    F     Cl      COCH.sub.3                                              6.02    F     Cl      COCH.sub.2 Cl                                           6.03    F     Cl      COCF.sub.3                                              6.04    F             COCH.sub.3                                              6.05    F     Cl      C(CH.sub.3)NOH                                          6.06    F     Cl      C(CH.sub.3)NOCH.sub.3                                   6.07    F     Cl      C(CN)NOH                                                6.08    F     Br      C(CN)NOC.sub.2 H.sub.5                                  6.09    F     Cl      C(CN)NOCH(CH.sub.3)COOCH.sub.3                          6.10    F     Cl                                                                                     ##STR51##                                              6.11    F     Cl                                                                                     ##STR52##                                              6.12    F     Cl                                                                                     ##STR53##                                              6.13    F     Cl      COOH                                                    6.14    F     Br      COOH                                                    6.15    F     Cl      COOCH.sub.3                                             6.16    F     Cl      COOCH(CH.sub.3).sub.2                                   6.17    H     Cl      COOH                                                    6.18    H     Cl      COOCH.sub.3                                             6.19    H     Cl      COOCH(CH.sub.3).sub.2                                   6.20    F     Cl      COSCH.sub.2 COOCH.sub.3                                 6.21    F     Cl      COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                6.22    F     Cl      COSCH.sub.2 (CH.sub.3)COOCH.sub.3                       6.23    F     Cl      COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                   6.24    F     Cl      OH                                                      6.25    F     Br      OH                                                      6.26    F     Cl      OCH.sub.3                                               6.27    F     Cl      OCH(CH.sub.3).sub.2 m.p. 71-73°                  6.28    F     Br      OCH.sub.2 CHCH.sub.2                                    6.29    F     Cl      OCH.sub.2 CHCHCl                                        6.30    F     Cl      OCH.sub.2 CClCH.sub.2                                   6.31    F     Cl      OCH.sub.2 COOCH.sub.3                                   6.32    F     Cl      OCH.sub.2 COOCH(CH.sub.3).sub.2                         6.33    F     Cl      SH                                                      6.34    F     Br      SH                                                      6.35    F     Cl      SCH.sub.3                                               6.36    F     Cl      SCH(CH.sub.3).sub.2                                     6.37    F     Cl      SCH.sub.2 CHCHCl                                        6.38    F     Cl      SCH.sub.2 COOH                                          6.39    F     Br      SCH.sub.2 COOH                                          6.40    F     Cl      SCH(CH.sub.3)COOH                                       6.41    F     Cl      SCH.sub.2 COOCH.sub.3                                   6.42    F     Cl      SCH(CH.sub.3)COOCH.sub.3                                6.43    F     Cl      OCH.sub.2 CCH                                           6.44    F     Cl      OCH(CH.sub.3)COOCH.sub.3                                ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                         ##STR54##                                                                    No.     R.sup.1                                                                             R.sup.2 A                                                       ______________________________________                                        7.01    F     Cl      COCH.sub.3                                              7.02    F     Cl      COCH.sub.2 Cl                                           7.03    F     Cl      COCF.sub.3                                              7.04    F             COCH.sub.3                                              7.05    F     Cl      C(CH.sub.3)NOH                                          7.06    F     Cl      C(CH.sub.3)NOCH.sub.3                                   7.07    F     Cl      C(CN)NOH                                                7.08    F     Br      C(CN)NOC.sub.2 H.sub.5                                  7.09    F     Cl      C(CN)NOCH(CH.sub.3)COOCH.sub.3                          7.10    F     Cl                                                                                     ##STR55##                                              7.11    F     Cl                                                                                     ##STR56##                                              7.12    F     Cl                                                                                     ##STR57##                                              7.13    F     Cl      COOH                                                    7.14    F     Br      COOH                                                    7.15    F     Cl      COOCH.sub.3                                             7.16    F     Cl      COOCH(CH.sub.3).sub.2                                   7.17    H     Cl      COOH                                                    7.18    H     Cl      COOCH.sub.3                                             7.19    H     Cl      COOCH(CH.sub.3).sub.2                                   7.20    F     Cl      COSCH.sub.2 COOCH.sub.3                                 7.21    F     Cl      COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                7.22    F     Cl      COSCH.sub.2 (CH.sub.3)COOCH.sub.3                       7.23    F     Cl      COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                   7.24    F     Cl      OH                                                      7.25    F     Br      OH                                                      7.26    F     Cl      OCH.sub.3                                               7.27    F     Cl      OCH(CH.sub.3).sub.2                                     7.28    F     Br      OCH.sub.2 CHCH.sub.2                                    7.29    F     Cl      OCH.sub.2 CHCHCl                                        7.30    F     Cl      OCH.sub.2 CClCH.sub.2                                   7.31    F     Cl      OCH.sub.2 COOCH.sub.3                                   7.32    F     Cl      OCH.sub.2 COOCH(CH.sub.3).sub.2                         7.33    F     Cl      SH                                                      7.34    F     Br      SH                                                      7.35    F     Cl      SCH.sub.3                                               7.36    F     Cl      SCH(CH.sub.3).sub.2                                     7.37    F     Cl      SCH.sub.2 CHCHCl                                        7.38    F     Cl      SCH.sub.2 COOH                                          7.39    F     Br      SCH.sub.2 COOH                                          7.40    F     Cl      SCH(CH.sub.3)COOH                                       7.41    F     Cl      SCH.sub.2 COOCH.sub.3                                   7.42    F     Cl      SCH(CH.sub.3)COOCH.sub.3                                7.43    F     Cl      OCH.sub.2 CCH                                           7.44    F     Cl      OCH(CH.sub.3)COOCH.sub.3                                ______________________________________                                    

                  TABLE 8                                                         ______________________________________                                         ##STR58##                                                                    No.     R.sup.1                                                                             R.sup.2 A                                                       ______________________________________                                        8.01    F     Cl      COCH.sub.3                                              8.02    F     Cl      COCH.sub.2 Cl                                           8.03    F     Cl      COCF.sub.3                                              8.04    F             COCH.sub.3                                              8.05    F     Cl      C(CH.sub.3)NOH                                          8.06    F     Cl      C(CH.sub.3)NOCH.sub.3                                   8.07    F     Cl      C(CN)NOH                                                8.08    F     Br      C(CN)NOC.sub.2 H.sub.5                                  8.09    F     Cl      C(CN)NOCH(CH.sub.3)COOCH.sub.3                          8.10    F     Cl                                                                                     ##STR59##                                              8.11    F     Cl                                                                                     ##STR60##                                              8.12    F     Cl                                                                                     ##STR61##                                              8.13    F     Cl      COOH                                                    8.14    F     Br      COOH                                                    8.15    F     Cl      COOCH.sub.3                                             8 16    F     Cl      COOCH(CH.sub.3).sub.2                                   8.17    H     Cl      COOH                                                    8.18    H     Cl      COOCH.sub.3                                             8.19    H     Cl      COOCH(CH.sub.3).sub.2                                   8.20    F     Cl      COSCH.sub.2 COOCH.sub.3                                 8.21    F     Cl      COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                8.22    F     Cl      COSCH.sub.2 (CH.sub.3)COOCH.sub.3                       8.23    F     Cl      COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                   8.24    F     Cl      OH                                                      8.25    F     Br      OH                                                      8.26    F     Cl      OCH.sub.3                                               8.27    F     Cl      OCH(CH.sub.3).sub.2 m.p. 119-120°                8.28    F     Br      OCH.sub.2 CHCH.sub.2                                    8.29    F     Cl      OCH.sub.2 CHCHCl                                        8.30    F     Cl      OCH.sub.2 CClCH.sub.2                                   8.31    F     Cl      OCH.sub.2 COOCH.sub.3                                   8.32    F     Cl      OCH.sub.2 COOCH(CH.sub.3).sub.2                         8.33    F     Cl      SH                                                      8.34    F     Br      SH                                                      8.35    F     Cl      SCH.sub.3                                               8.36    F     Cl      SCH(CH.sub.3).sub.2                                     8.37    F     Cl      SCH.sub.2 CH CHCl                                       8.38    F     Cl      SCH.sub.2 COOH                                          8.39    F     Br      SCH.sub.2 COOH                                          8.40    F     Cl      SCH(CH.sub.3)COOH                                       8.41    F     Cl      SCH.sub.2 COOCH.sub.3                                   8.42    F     Cl      SCH(CH.sub.3)COOCH.sub.3                                8.43    F     Cl      OCH.sub.2 CCH                                           8.44    F     Cl      OCH(CH.sub.3)COOCH.sub.3                                ______________________________________                                    

                  TABLE 9                                                         ______________________________________                                         ##STR62##                                                                    No.   R.sup.1                                                                             R.sup.2 A                                                         ______________________________________                                        9.01  F     Cl      COCH.sub.3                                                9.02  F     Cl      COCH.sub.2 Cl                                             9.03  F     Cl      COCF.sub.3                                                9.04  F             COCH.sub.3                                                9.05  F     Cl      C(CH.sub.3)NOH                                            9.06  F     Cl      C(CH.sub.3)NOCH.sub.3                                     9.07  F     Cl      C(CN)NOH                                                  9.08  F     Br      C(CN)NOC.sub.2 H.sub.5                                    9.09  F     Cl      C(CN)NOCH(CH.sub.3)COOCH.sub.3                            9.10  F     Cl                                                                                     ##STR63##                                                9.11  F     Cl                                                                                     ##STR64##                                                9.12  F     Cl                                                                                     ##STR65##                                                9.13  F     Cl      COOH                                                      9.14  F     Br      COOH                                                      9.15  F     Cl      COOCH.sub.3                                               9.16  F     Cl      COOCH(CH.sub.3).sub.2                                     9.17  H     Cl      COOH                                                      9.18  H     Cl      COOCH.sub.3                                               9.19  H     Cl      COOCH(CH.sub.3).sub.2                                     9.20  F     Cl      COSCH.sub.2 COOCH.sub.3                                   9.21  F     Cl      COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                  9.22  F     Cl      COSCH.sub.2 (CH.sub.3)COOCH.sub.3                         9.23  F     Cl      COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                     9.24  F     Cl      OH                                                        9.25  F     Br      OH                                                        9.26  F     Cl      OCH.sub.3                                                 9.27  F     Cl      OCH(CH.sub.3).sub.2 oil                                   9.28  F     Br      OCH.sub.2 CHCH.sub.2                                      9.29  F     Cl      OCH.sub.2 CHCHCl                                          9.30  F     Cl      OCH.sub.2 CClCH.sub.2                                     9.31  F     Cl      OCH.sub.2 COOCH.sub.3                                     9.32  F     Cl      OCH.sub.2 COOCH(CH.sub.3).sub.2                           9.33  F     Cl      SH                                                        9.34  F     Br      SH                                                        9.35  F     Cl      SCH.sub.3                                                 9.36  F     Cl      SCH(CH.sub.3).sub.2                                       9.37  F     Cl      SCH.sub.2 CHCHCl                                          9.38  F     Cl      SCH.sub.2 COOH                                            9.39  F     Br      SCH.sub.2 COOH                                            9.40  F     Cl      SCH(CH.sub.3)COOH                                         9.41  F     Cl      SCH.sub.2 COOCH.sub.3                                     9.42  F     Cl      SCH(CH.sub.3)COOCH.sub.3                                  9.43  F     Cl      OCH.sub.2 CCH                                             9.44  F     Cl      OCH(CH.sub.3)COOCH.sub.3                                  ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                         ##STR66##                                                                    No.     R.sup.1                                                                             R.sup.2  A                                                      ______________________________________                                        10.01   F     Cl       COCH.sub.3                                             10.02   F     Cl       COCH.sub.2 Cl                                          10.03   F     Cl       COCF.sub.3                                             10.04   F              COCH.sub.3                                             10.05   F     Cl       C(CH.sub.3)NOH                                         10.06   F     Cl       C(CH.sub.3)NOCH.sub.3                                  10.07   F     Cl       C(CN)NOH                                               10.08   F     Br       C(CN)NOC.sub.2 H.sub.5                                 10.09   F     Cl       C(CN)NOCH(CH.sub.3)COOCH.sub.3                         10.10   F     Cl                                                                                      ##STR67##                                             10.11   F     Cl                                                                                      ##STR68##                                             10.12   F     Cl                                                                                      ##STR69##                                             10.13   F     Cl       COOH                                                   10.14   F     Br       COOH                                                   10.15   F     Cl       COOCH.sub.3                                            10.16   F     Cl       COOCH(CH.sub.3).sub.2                                  10.17   H     Cl       COOH                                                   10.18   H     Cl       COOCH.sub.3                                            10.19   H     Cl       COOCH(CH.sub.3).sub.2                                  10.20   F     Cl       COSCH.sub.2 COOCH.sub.3                                10.21   F     Cl       COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2               10.22   F     Cl       COSCH.sub.2 (CH.sub.3)COOCH.sub.3                      10.23   F     Cl       COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                  10.24   F     Cl       OH                                                     10.25   F     Br       OH                                                     10.26   F     Cl       OCH.sub.3                                              10.27   F     Cl       OCH(CH.sub.3).sub.2                                    10.28   F     Br       OCH.sub.2 CHCH.sub.2                                   10.29   F     Cl       OCH.sub.2 CHCHCl                                       10.30   F     Cl       OCH.sub.2 CClCH.sub.2                                  10.31   F     Cl       OCH.sub.2 COOCH.sub.3                                  10.32   F     Cl       OCH.sub.2 COOCH(CH.sub.3).sub.2                        10.33   F     Cl       SH                                                     10.34   F     Br       SH                                                     10.35   F     Cl       SCH.sub.3                                              10.36   F     Cl       SCH(CH.sub.3).sub.2                                    10.37   F     Cl       SCH.sub.2 CHCHCl                                       10.38   F     Cl       SCH.sub.2 COOH                                         10.39   F     Br       SCH.sub.2 COOH                                         10.40   F     Cl       SCH(CH.sub.3)COOH                                      10.41   F     Cl       SCH.sub.2 COOCH.sub.3                                  10.42   F     Cl       SCH(CH.sub.3)COOCH.sub.3                               10.43   F     Cl       OCH.sub.2 CCH                                          10.44   F     Cl       OCH(CH.sub.3)COOCH.sub.3                               ______________________________________                                    

                  TABLE 11                                                        ______________________________________                                         ##STR70##                                                                    No.   R.sup.1                                                                             R.sup.2                                                                             A                                                           ______________________________________                                        11.01 F     Cl    COCH.sub.3                                                  11.02 F     Cl    COCH.sub.2 Cl                                               11.03 F     Cl    COCF.sub.3                                                  11.04 F           COCH.sub.3                                                  11.05 F     Cl    C(CH.sub.3)NOH                                              11.06 F     Cl    C(CH.sub.3)NOCH.sub.3                                       11.07 F     Cl    C(CN)NOH                                                    11.08 F     Br    C(CN)NOC.sub.2 H.sub.5                                      11.09 F     Cl    C(CN)NOCH(CH.sub.3)COOCH.sub.3                              11.10 F     Cl                                                                                   ##STR71##                                                  11.11 F     Cl                                                                                   ##STR72##                                                  11.12 F     Cl                                                                                   ##STR73##                                                  11.13 F     Cl    COOH                                                        11.14 F     Br    COOH                                                        11.15 F     Cl    COOCH.sub.3                                                 11.16 F     Cl    COOCH(CH.sub.3).sub.2                                       11.17 H     Cl    COOH                                                        11.18 H     Cl    COOCH.sub.3                                                 11.19 H     Cl    COOCH(CH.sub.3).sub.2                                       11.20 F     Cl    COSCH.sub.2 COOCH.sub.3                                     11.21 F     Cl    COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                    11.22 F     Cl    COSCH.sub.2 (CH.sub.3)COOCH.sub.3                           11.23 F     Cl    COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                       11.24 F     Cl    OH                                                          11.25 F     Br    OH                                                          11.26 F     Cl    OCH.sub.3                                                   11.27 F     Cl    OCH(CH.sub.3).sub.2                                                                              m.p. 68-70°                       11.28 F     Br    OCH.sub.2 CHCH.sub.2                                        11.29 F     Cl    OCH.sub.2 CHCHCl                                            11.30 F     Cl    OCH.sub.2 CClCH.sub.2                                       11.31 F     Cl    OCH.sub.2 COOCH.sub.3                                       11.32 F     Cl    OCH.sub.2 COOCH(CH.sub.3).sub.2                             11.33 F     Cl    SH                                                          11.34 F     Br    SH                                                          11.35 F     Cl    SCH.sub.3                                                   11.36 F     Cl    SCH(CH.sub.3).sub.2                                         11.37 F     Cl    SCH.sub.2 CHCHCl                                            11.38 F     Cl    SCH.sub.2 COOH                                              11.39 F     Br    SCH.sub.2 COOH                                              11.40 F     Cl    SCH(CH.sub.3)COOH                                           11.41 F     Cl    SCH.sub.2 COOCH.sub.3                                       11.42 F     Cl    SCH(CH.sub.3)COOCH.sub.3                                    11.43 F     Cl    OCH.sub.2 CCH                                               11.44 F     Cl    OCH(CH.sub.3)COOCH.sub.3                                    ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                         ##STR74##                                                                    No.     R.sup.1                                                                             R.sup.2  A                                                      ______________________________________                                        12.01   F     Cl       COCH.sub.3                                             12.02   F     Cl       COCH.sub.2 Cl                                          12.03   F     Cl       COCF.sub.3                                             12.04   F              COCH.sub.3                                             12.05   F     Cl       C(CH.sub.3)NOH                                         12.06   F     Cl       C(CH.sub.3)NOCH.sub.3                                  12.07   F     Cl       C(CN)NOH                                               12.08   F     Br       C(CN)NOC.sub.2 H.sub.5                                 12.09   F     Cl       C(CN)NOCH(CH.sub.3)COOCH.sub.3                         12.10   F     Cl                                                                                      ##STR75##                                             12.11   F     Cl                                                                                      ##STR76##                                             12.12   F     Cl                                                                                      ##STR77##                                             12.13   F     Cl       COOH                                                   12.14   F     Br       COOH                                                   12.15   F     Cl       COOCH.sub.3                                            12.16   F     Cl       COOCH(CH.sub.3).sub.2                                  12.17   H     Cl       COOH                                                   12.18   H     Cl       COOCH.sub.3                                            12.19   H     Cl       COOCH(CH.sub.3).sub.2                                  12.20   F     Cl       COSCH.sub.2 COOCH.sub.3                                12.21   F     Cl       COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2               12.22   F     Cl       COSCH.sub.2 (CH.sub.3)COOCH.sub.3                      12.23   F     Cl       COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                  12.24   F     Cl       OH                                                     12.25   F     Br       OH                                                     12.26   F     Cl       OCH.sub.3                                              12.27   F     Cl       OCH(CH.sub.3).sub.2                                    12.28   F     Br       OCH.sub.2 CHCH.sub.2                                   12.29   F     Cl       OCH.sub.2 CHCHCl                                       12.30   F     Cl       OCH.sub.2 CClCH.sub.2                                  12.31   F     Cl       OCH.sub.2 COOCH.sub.3                                  12.32   F     Cl       OCH.sub.2 COOCH(CH.sub.3).sub.2                        12.33   F     Cl       SH                                                     12.34   F     Br       SH                                                     12.35   F     Cl       SCH.sub.3                                              12.36   F     Cl       SCH(CH.sub.3).sub.2                                    12.37   F     Cl       SCH.sub.2 CHCHCl                                       12.38   F     Cl       SCH.sub.2 COOH                                         12.39   F     Br       SCH.sub.2 COOH                                         12.40   F     Cl       SCH(CH.sub.3)COOH                                      12.41   F     Cl       SCH.sub.2 COOCH.sub.3                                  12.42   F     Cl       SCH(CH.sub.3)COOCH.sub.3                               12.43   F     Cl       OCH.sub.2 CCH                                          12.44   F     Cl       OCH(CH.sub.3)COOCH.sub.3                               ______________________________________                                    

                  TABLE 13                                                        ______________________________________                                          #STR78##                                                                    No.  R.sup.1                                                                             R.sup.2                                                                             A                                                            ______________________________________                                        13.01                                                                              F     Cl    COCH.sub.3                                                   13.02                                                                              F     Cl    COCH.sub.2 Cl                                                13.03                                                                              F     Cl    COCF.sub.3                                                   13.04                                                                              F           COCH.sub.3                                                   13.05                                                                              F     Cl    C(CH.sub.3)NOH                                               13.06                                                                              F     Cl    C(CH.sub.3)NOCH.sub.3                                        13.07                                                                              F     Cl    C(CN)NOH                                                     13.08                                                                              F     Br    C(CN)NOC.sub.2 H.sub.5                                       13.09                                                                              F     Cl    C(CN)NOCH(CH.sub.3)COOCH.sub.3                               13.10                                                                              F     Cl                                                                                   ##STR79##                                                   13.11                                                                              F     Cl                                                                                   ##STR80##                                                   13.12                                                                              F     Cl                                                                                   ##STR81##                                                   13.13                                                                              F     Cl    COOH                                                         13.14                                                                              F     Br    COOH                                                         13.15                                                                              F     Cl    COOCH.sub.3                                                  13.16                                                                              F     Cl    COOCH(CH.sub.3).sub.2                                        13.17                                                                              H     Cl    COOH                                                         13.18                                                                              H     Cl    COOCH.sub.3                                                  13.19                                                                              H     Cl    COOCH(CH.sub.3).sub.2                                        13.20                                                                              F     Cl    COSCH.sub.2 COOCH.sub.3                                      13.21                                                                              F     Cl    COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                     13.22                                                                              F     Cl    COSCH.sub.2 (CH.sub.3)COOCH.sub.3                            13.23                                                                              F     Cl    COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                        13.24                                                                              F     Cl    OH                                                           13.25                                                                              F     Br    OH                                                           13.26                                                                              F     Cl    OCH.sub.3                                                    13.27                                                                              F     Cl    OCH(CH.sub.3).sub.2                                          13.28                                                                              F     Br    OCH.sub.2 CHCH.sub.2                                         13.29                                                                              F     Cl    OCH.sub.2 CHCHCl                                             13.30                                                                              F     Cl    OCH.sub.2 CClCH.sub.2                                        13.31                                                                              F     Cl    OCH.sub.2 COOCH.sub.3                                        13.32                                                                              F     Cl    OCH.sub.2 COOCH(CH.sub.3).sub.2                              13.33                                                                              F     Cl    SH                                                           13.34                                                                              F     Br    SH                                                           13.35                                                                              F     Cl    SCH.sub.3                                                    13.36                                                                              F     Cl    SCH(CH.sub.3).sub.2                                          13.37                                                                              F     Cl    SCH.sub.2 CHCHCl                                             13.38                                                                              F     Cl    SCH.sub.2 COOH                                               13.39                                                                              F     Br    SCH.sub.2 COOH                                               13.40                                                                              F     Cl    SCH(CH.sub.3)COOH                                            13.41                                                                              F     Cl    SCH.sub.2 COOCH.sub.3                                        13.42                                                                              F     Cl    SCH(CH.sub.3)COOCH.sub.3                                     13.43                                                                              H     Cl    H                  m.p. 101-102°                      13.44                                                                              H     Br    H                                                            13.45                                                                              F     Cl    OC.sub.2 H.sub.5                                             13.46                                                                              F     Cl    OC.sub.3 H.sub.7n                                            13.47                                                                              F     Cl    OC.sub.4 H.sub.9n                                            13.48                                                                              F     Cl    OCH(CH.sub.3)C.sub.2 H.sub.5                                 13.49                                                                              F     Cl    OCH.sub.2 CH(CH.sub.3).sub.2                                 13.50                                                                              F     Cl    OCH.sub.2 CCH      n.sub.D.sup.22 = 1,5363                   13.51                                                                              F     Cl    OCH(CH.sub.3)COOCH.sub.3                                     ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                         ##STR82##                                                                    No.  R.sup.1                                                                             R.sup.2                                                                             A                                                            ______________________________________                                        14.01                                                                              F     Cl    COCH.sub.3                                                   14.02                                                                              F     Cl    COCH.sub.2 Cl                                                14.03                                                                              F     Cl    COCF.sub.3                                                   14.04                                                                              F           COCH.sub.3                                                   14.05                                                                              F     Cl    C(CH.sub.3)NOH                                               14.06                                                                              F     Cl    C(CH.sub.3)NOCH.sub.3                                        14.07                                                                              F     Cl    C(CN)NOH                                                     14.08                                                                              F     Br    C(CN)NOC.sub.2 H.sub.5                                       14.09                                                                              F     Cl    C(CN)NOCH(CH.sub.3)COOCH.sub.3                               14.10                                                                              F     Cl                                                                                   ##STR83##                                                   14.11                                                                              F     Cl                                                                                   ##STR84##                                                   14.12                                                                              F     Cl                                                                                   ##STR85##                                                   14.13                                                                              F     Cl    COOH                                                         14.14                                                                              F     Br    COOH                                                         14.15                                                                              F     Cl    COOCH.sub.3                                                  14.16                                                                              F     Cl    COOCH(CH.sub.3).sub.2                                        14.17                                                                              H     Cl    COOH                                                         14.18                                                                              H     Cl    COOCH.sub.3                                                  14.19                                                                              H     Cl    COOCH(CH.sub.3).sub.2                                        14.20                                                                              F     Cl    COSCH.sub.2 COOCH.sub.3                                      14.21                                                                              F     Cl    COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                     14.22                                                                              F     Cl    COSCH.sub.2 (CH.sub.3)COOCH.sub.3                            14.23                                                                              F     Cl    COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                        14.24                                                                              F     Cl    OH                                                           14.25                                                                              F     Br    OH                                                           14.26                                                                              F     Cl    OCH.sub.3                                                    14.27                                                                              F     Cl    OCH(CH.sub.3).sub.2                                                                              n.sub.D.sup.22 = 1.5185                   14.28                                                                              F     Br    OCH.sub.2 CHCH.sub.2                                         14.29                                                                              F     Cl    OCH.sub.2 CHCHCl                                             14.30                                                                              F     Cl    OCH.sub.2 CClCH.sub.2                                        14.31                                                                              F     Cl    OCH.sub.2 COOCH.sub.3                                        14.32                                                                              F     Cl    OCH.sub.2 COOCH(CH.sub.3).sub.2                              14.33                                                                              F     Cl    SH                                                           14.34                                                                              F     Br    SH                                                           14.35                                                                              F     Cl    SCH.sub.3                                                    14.36                                                                              F     Cl    SCH(CH.sub.3).sub.2                                          14.37                                                                              F     Cl    SCH.sub.2 CHCHCl                                             14.38                                                                              F     Cl    SCH.sub.2 COOH                                               14.39                                                                              F     Br    SCH.sub.2 COOH                                               14.40                                                                              F     Cl    SCH(CH.sub.3)COOH                                            14.41                                                                              F     Cl    SCH.sub.2 COOCH.sub.3                                        14.42                                                                              F     Cl    SCH(CH.sub.3)COOCH.sub.3                                     14.43                                                                              H     Cl    H                  m.p. 195-196°                      14.44                                                                              F     Cl    OCH.sub.2 CCH                                                14.45                                                                              F     Cl    OCH(CH.sub.3)COOCH.sub.3                                     ______________________________________                                    

                  TABLE 15                                                        ______________________________________                                         ##STR86##                                                                    No.     R.sup.1                                                                             R.sup.2  A                                                      ______________________________________                                        15.01   F     Cl       COCH.sub.3                                             15.02   F     Cl       COCH.sub.2 Cl                                          15.03   F     Cl       COCF.sub.3                                             15.04   F              COCH.sub.3                                             15.05   F     Cl       C(CH.sub.3)NOH                                         15.06   F     Cl       C(CH.sub.3)NOCH.sub.3                                  15.07   F     Cl       C(CN)NOH                                               15.08   F     Br       C(CN)NOC.sub.2 H.sub.5                                 15.09   F     Cl       C(CN)NOCH(CH.sub.3)COOCH.sub.3                         15.10   F     Cl                                                                                      ##STR87##                                             15.11   F     Cl                                                                                      ##STR88##                                             15.12   F     Cl                                                                                      ##STR89##                                             15.13   F     Cl       COOH                                                   15.14   F     Br       COOH                                                   15.15   F     Cl       COOCH.sub.3                                            15.16   F     Cl       COOCH(CH.sub.3).sub.2                                  15.17   H     Cl       COOH                                                   15.18   H     Cl       COOCH.sub.3                                            15.19   H     Cl       COOCH(CH.sub.3).sub.2                                  15.20   F     Cl       COSCH.sub.2 COOCH.sub.3                                15.21   F     Cl       COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2               15.22   F     Cl       COSCH.sub.2 (CH.sub.3)COOCH.sub.3                      15.23   F     Cl       COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                  15.24   F     Cl       OH                                                     15.25   F     Br       OH                                                     15.26   F     Cl       OCH.sub.3                                              15.27   F     Cl       OCH(CH.sub.3).sub.2                                    15.28   F     Br       OCH.sub.2 CHCH.sub.2                                   15.29   F     Cl       OCH.sub.2 CHCHCl                                       15.30   F     Cl       OCH.sub.2 CClCH.sub.2                                  15.31   F     Cl       OCH.sub.2 COOCH.sub.3                                  15.32   F     Cl       OCH.sub.2 COOCH(CH.sub.3).sub.2                        15.33   F     Cl       SH                                                     15.34   F     Br       SH                                                     15.35   F     Cl       SCH.sub.3                                              15.36   F     Cl       SCH(CH.sub.3).sub.2                                    15.37   F     Cl       SCH.sub.2 CHCHCl                                       15.38   F     Cl       SCH.sub. 2 COOH                                        15.39   F     Br       SCH.sub.2 COOH                                         15.40   F     Cl       SCH(CH.sub.3)COOH                                      15.41   F     Cl       SCH.sub.2 COOCH.sub.3                                  15.42   F     Cl       SCH(CH.sub.3)COOCH.sub.3                               15.43   F     Cl       OCH.sub.2 CCH                                          15.44   F     Cl       OCH(CH.sub.3)COOCH.sub.3                               ______________________________________                                    

                  TABLE 16                                                        ______________________________________                                         ##STR90##                                                                    No.  R.sup.1                                                                             R.sup.2                                                                             A                                                            ______________________________________                                        16.01                                                                              F     Cl    COCH.sub.3                                                   16.02                                                                              F     Cl    COCH.sub.2 Cl                                                16.03                                                                              F     Cl    COCF.sub.3                                                   16.04                                                                              F           COCH.sub.3                                                   16.05                                                                              F     Cl    C(CH.sub.3)NOH                                               16.06                                                                              F     Cl    C(CH.sub.3)NOCH.sub.3                                        16.07                                                                              F     Cl    C(CN)NOH                                                     16.08                                                                              F     Br    C(CN)NOC.sub.2 H.sub.5                                       16.09                                                                              F     Cl    C(CN)NOCH(CH.sub.3)COOCH.sub.3                               16.10                                                                              F     Cl                                                                                   ##STR91##                                                   16.11                                                                              F     Cl                                                                                   ##STR92##                                                   16.12                                                                              F     Cl                                                                                   ##STR93##                                                   16.13                                                                              F     Cl    COOH                                                         16.14                                                                              F     Br    COOH                                                         16.15                                                                              F     Cl    COOCH.sub.3                                                  16.16                                                                              F     Cl    COOCH(CH.sub.3).sub.2                                        16.17                                                                              H     Cl    COOH                                                         16.18                                                                              H     Cl    COOCH.sub.3                                                  16.19                                                                              H     Cl    COOCH(CH.sub.3).sub.2                                        16.20                                                                              F     Cl    COSCH.sub.2 COOCH.sub.3                                      16.21                                                                              F     Cl    COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                     16.22                                                                              F     Cl    COSCH.sub.2 (CH.sub.3)COOCH.sub.3                            16.23                                                                              F     Cl    COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                        16.24                                                                              F     Cl    OH                                                           16.25                                                                              F     Br    OH                                                           16.26                                                                              F     Cl    OCH.sub.3                                                    16.27                                                                              F     Cl    OCH(CH.sub.3).sub.2                                                                              n.sub.D.sup.22 = 1.5229                   16.28                                                                              F     Br    OCH.sub.2 CHCH.sub.2                                         16.29                                                                              F     Cl    OCH.sub.2 CHCHCl                                             16.30                                                                              F     Cl    OCH.sub.2 CClCH.sub.2                                        16.31                                                                              F     Cl    OCH.sub.2 COOCH.sub.3                                        16.32                                                                              F     Cl    OCH.sub.2 COOCH(CH.sub.3).sub.2                              16.33                                                                              F     Cl    SH                                                           16.34                                                                              F     Br    SH                                                           16.35                                                                              F     Cl    SCH.sub.3                                                    16.36                                                                              F     Cl    SCH(CH.sub.3).sub.2                                          16.37                                                                              F     Cl    SCH.sub.2 CHCHCl                                             16.38                                                                              F     Cl    SCH.sub.2 COOH                                               16.39                                                                              F     Br    SCH.sub.2 COOH                                               16.40                                                                              F     Cl    SCH(CH.sub.3)COOH                                            16.41                                                                              F     Cl    SCH.sub.2 COOCH.sub.3                                        16.42                                                                              F     Cl    SCH(CH.sub.3)COOCH.sub.3                                     16.43                                                                              F     Cl    OCH.sub.2 CCH                                                16.44                                                                              F     Cl    OCH(CH.sub.3)COOCH.sub.3                                     ______________________________________                                    

                  TABLE 17                                                        ______________________________________                                         ##STR94##                                                                    No.    R.sup.1                                                                             R.sup.2 A                                                        ______________________________________                                        17.01  F     Cl      COCH.sub.3                                               17.02  F     Cl      COCH.sub.2 Cl                                            17.03  F     Cl      COCF.sub.3                                               17.04  F             COCH.sub.3                                               17.05  F     Cl      C(CH.sub.3)NOH                                           17.06  F     Cl      C(CH.sub.3)NOCH.sub.3                                    17.07  F     Cl      C(CN)NOH                                                 17.08  F     Br      C(CN)NOC.sub.2 H.sub.5                                   17.09  F     Cl      C(CN)NOCH(CH.sub.3)COOCH.sub.3                           17.10  F     Cl                                                                                     ##STR95##                                               17.11  F     Cl                                                                                     ##STR96##                                               17.12  F     Cl                                                                                     ##STR97##                                               17.13  F     Cl      COOH                                                     17.14  F     Br      COOH                                                     17.15  F     Cl      COOCH.sub.3                                              17.16  F     Cl      COOCH(CH.sub.3).sub.2                                    17.17  H     Cl      COOH                                                     17.18  H     Cl      COOCH.sub.3                                              17.19  H     Cl      COOCH(CH.sub.3).sub.2                                    17.20  F     Cl      COSCH.sub.2 COOCH.sub.3                                  17.21  F     Cl      COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                 17.22  F     Cl      COSCH.sub.2 (CH.sub.3)COOCH.sub.3                        17.23  F     Cl      COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                    17.24  F     Cl      OH                                                       17.25  F     Br      OH                                                       17.26  F     Cl      OCH.sub.3                                                17.27  F     Cl      OCH(CH.sub.3).sub.2                                      17.28  F     Br      OCH.sub.2 CHCH.sub.2                                     17.29  F     Cl      OCH.sub.2 CHCHCl                                         17.30  F     Cl      OCH.sub.2 CClCH.sub.2                                    17.31  F     Cl      OCH.sub.2 COOCH.sub.3                                    17.32  F     Cl      OCH.sub.2 COOCH(CH.sub.3).sub.2                          17.33  F     Cl      SH                                                       17.34  F     Br      SH                                                       17.35  F     Cl      SCH.sub.3                                                17.36  F     Cl      SCH(CH.sub.3).sub.2                                      17.37  F     Cl      SCH.sub.2 CHCHCl                                         17.38  F     Cl      SCH.sub.2 COOH                                           17.39  F     Br      SCH.sub.2 COOH                                           17.40  F     Cl      SCH(CH.sub.3)COOH                                        17.41  F     Cl      SCH.sub.2 COOCH.sub.3                                    17.42  F     Cl      SCH(CH.sub.3)COOCH.sub.3                                 17.43  F     Cl      H                  oil                                   17.44  F     Cl      OCH.sub.2 CCH                                            17.45  F     Cl      OCH(CH.sub.3)COOCH.sub.3                                 ______________________________________                                    

                  TABLE 18                                                        ______________________________________                                         ##STR98##                                                                    No.  R.sup.1                                                                             R.sup.2                                                                              A                                                           ______________________________________                                        18.01                                                                              F     Cl     COCH.sub.3                                                  18.02                                                                              F     Cl     COCH.sub.2 Cl                                               18.03                                                                              F     Cl     COCF.sub.3                                                  18.04                                                                              F            COCH.sub.3                                                  18.05                                                                              F     Cl     C(CH.sub.3)NOH                                              18.06                                                                              F     Cl     C(CH.sub.3)NOCH.sub.3                                       18.07                                                                              F     Cl     C(CN)NOH                                                    18.08                                                                              F     Br     C(CN)NOC.sub.2 H.sub.5                                      18.09                                                                              F     Cl     C(CN)NOCH(CH.sub.3)COOCH.sub.3                              18.10                                                                              F     Cl                                                                                    ##STR99##                                                  18.11                                                                              F     Cl                                                                                    ##STR100##                                                 18.12                                                                              F     Cl                                                                                    ##STR101##                                                 18.13                                                                              F     Cl     COOH                                                        18.14                                                                              F     Br     COOH                                                        18.15                                                                              F     Cl     COOCH.sub.3                                                 18.16                                                                              F     Cl     COOCH(CH.sub.3).sub.2                                       18.17                                                                              H     Cl     COOH                                                        18.18                                                                              H     Cl     COOCH.sub.3                                                 18.19                                                                              H     Cl     COOCH(CH.sub.3).sub.2                                       18.20                                                                              F     Cl     COSCH.sub.2 COOCH.sub.3                                     18.21                                                                              F     Cl     COSCH.sub.2 COOCH.sub.2 (CH.sub.3).sub.2                    18.22                                                                              F     Cl     COSCH.sub.2 (CH.sub.3)COOCH.sub.3                           18.23                                                                              F     Cl     COSCH(CH.sub.3)COOCH.sub.2 CHCH.sub.2                       18.24                                                                              F     Cl     OH                                                          18.25                                                                              F     Br     OH                                                          18.26                                                                              F     Cl     OCH.sub.3                                                   18.27                                                                              F     Cl     OCH(CH.sub.3).sub.2                                                                              m.p. 80-81°                       18.28                                                                              F     Br     OCH.sub.2 CHCH.sub.2                                        18.29                                                                              F     Cl     OCH.sub.2 CHCHCl                                            18.30                                                                              F     Cl     OCH.sub.2 CClCH.sub.2                                       18.31                                                                              F     Cl     OCH.sub.2 COOCH.sub.3                                       18.32                                                                              F     Cl     OCH.sub.2 COOCH(CH.sub.3).sub.2                             18.33                                                                              F     Cl     SH                                                          18.34                                                                              F     Br     SH                                                          18.35                                                                              F     Cl     SCH.sub.3                                                   18.36                                                                              F     Cl     SCH(CH.sub.3).sub.2                                         18.37                                                                              F     Cl     SCH.sub. 2 CHCHCl                                           18.38                                                                              F     Cl     SCH.sub.2 COOH                                              18.39                                                                              F     Br     SCH.sub.2 COOH                                              18.40                                                                              F     Cl     SCH(CH.sub.3)COOH                                           18.41                                                                              F     Cl     SCH.sub.2 COOCH.sub.3                                       18.42                                                                              F     Cl     SCH(CH.sub.3)COOCH.sub.3                                    18.43                                                                              F     Cl     H                  m.p. 89-93°                       18.44                                                                              F     Cl     OCH.sub.2 CCH                                               18.45                                                                              F     Cl     OCH(CH.sub.3)COOCH.sub.3                                    ______________________________________                                    

FORMULATION EXAMPLES EXAMPLE 15 Formulation Examples for liquid activeingredients of the formula I (%=percent by weight)

    ______________________________________                                        (a) emulsifiable concentrates                                                                    (a)       (b)    (c)                                       ______________________________________                                        active ingredient according                                                                       20%      40%    50%                                       to Tables 1-10                                                                calcium dodecylbenzene-                                                                            5%       8%    5.8%                                      sulphonate                                                                    castor oil polyethylene glycol                                                                     5%      --     --                                        ether (36 moles of ethylene oxide)                                            tributylphenoyl polyethylene                                                                      --       12%    4.2%                                      glycol ether (30 moles of                                                     ethylene oxide)                                                               cyclohexanone       --       15%    20%                                       xylene mixture      70%      25%    20%                                       ______________________________________                                    

Emulsions of any desired concentration can be prepared from theseconcentrates by dilution with water.

    ______________________________________                                        (b) solutions    (a)    (b)      (c)  (d)                                     ______________________________________                                        active ingredient according                                                                    80%    10%       5%  95%                                     to Tables 1-10                                                                ethylene glycol monomethyl                                                                     20%    --       --   --                                      ether                                                                         polyethylene glycol MW 400                                                                     --     70%      --   --                                      N--methyl-2-pyrrolidone                                                                        --     20%      --   --                                      epoxidised coconut oil                                                                         --     --       94%  --                                      ______________________________________                                    

The solutions are suitable for use in the form of very fine droplets.

    ______________________________________                                        (c) granulates      (a)     (b)                                               ______________________________________                                        active ingredient according                                                                       5%      10%                                               to Tables 1-10                                                                kaolin              94%     --                                                highly dispersed silicic acid                                                                     1%                                                        attapulgite         --      90%                                               ______________________________________                                    

The active ingredient is dissolved in methylene chloride, sprayed ontothe carrier and the solvent is then evaporated off in vacuo.

    ______________________________________                                        (d) dusts           (a)     (b)                                               ______________________________________                                        active ingredient according                                                                       2%      5%                                                to Tables 1-10                                                                highly dispersed silicic acid                                                                     1%      5%                                                talcum              97%     --                                                kaolin              --      90%                                               ______________________________________                                    

Dusts that are ready for use are obtained by intimately mixing thecarriers with the active ingredient.

EXAMPLE 16 Formulation Examples for solid active ingredients of theformula I (%=percent by weight)

    ______________________________________                                        (a) wettable powders   (a)    (b)                                             ______________________________________                                        active ingredient according                                                                          20%    60%                                             to Tables 1-10                                                                sodium lignosulphonate  5%    5%                                              sodium lauryl sulphate --     6%                                              octylphenolpolyethylene glycol                                                                       --     2%                                              ether (7-8 moles of ethylene oxide)                                           highly dispersed silicic acid                                                                         5%    27%                                             kaolin                 67%    --                                              ______________________________________                                    

The active ingredient is mixed well with the additives and ground wellin a suitable mill. A wettable powder is obtained which can be dilutedwith water to form a suspension of any desired concentration.

    ______________________________________                                        (b) emulsifiable concentrate                                                  ______________________________________                                        active ingredient according to                                                                       10%                                                    Tables 1-10                                                                   octylphenolpolyethylene gycol                                                                         3%                                                    ether (4-5 moles of ethylene oxide)                                           calcium dodecylbenzenesulphonate                                                                      3%                                                    castor oil polyglycol ether                                                                           4%                                                    (36 moles of ethylene oxide)                                                  cyclohexanone          30%                                                    xylene mixture         50%                                                    ______________________________________                                    

Emulsions of any desired concentration can be prepared from thisconcentrate by dilution with water.

    ______________________________________                                        (c) dusts            (a)    (b)                                               ______________________________________                                        active ingredient according                                                                         5%     8%                                               to Tables 1-10                                                                talcum               95%    --                                                kaolin               --     92%                                               ______________________________________                                    

Dusts which are ready for use are obtained by mixing the activeingredient with the carrier and grinding them in a suitable mill.

    ______________________________________                                        (d) extruder granulate                                                        ______________________________________                                        active ingredient according                                                                       10%                                                       to Tables 1-10                                                                sodium lignosulphonate                                                                             2%                                                       carboxymethylcellulose                                                                             1%                                                       kaolin              87%                                                       ______________________________________                                    

The active ingredient is mixed with the additives, ground and moistenedwith water. This mixture is extruded and subsequently dried in a streamof air.

    ______________________________________                                        (e) coated granulate (encapsulated granulate?)                                ______________________________________                                        active ingredient according                                                                        3%                                                       to Tables 1-10                                                                polyethylene glycol (MW 200)                                                                       3%                                                       kaolin               94%                                                      ______________________________________                                    

The finely ground active ingredient is uniformly applied in a mixer tothe kaolin moistened with the polyethylene glycol. Dust-free coatedgranulates are obtained in this manner.

    ______________________________________                                        (f) suspension concentrate                                                    ______________________________________                                        active ingredient according                                                                          40%                                                    to Tables 1-10                                                                ethylene glycol        10%                                                    nonylphenolpolyethylene glycol                                                                        6%                                                    ether (15 moles of ethylene oxide)                                            sodium lignosulphonate 10%                                                    carboxymethylcellulose  1%                                                    37% aqueous formaldehyde solution                                                                    0.2%                                                   silicone oil in the form of a 75%                                                                    0.8%                                                   aqueous emulsion                                                              water                  32%                                                    ______________________________________                                    

The finely ground active ingredient is intimately mixed with theadditives. In this manner, a suspension concentrate is obtained fromwhich suspensions of any desired concentration can be prepared bydilution with water.

BIOLOGICAL EXAMPLES EXAMPLE 17 Pre-emergence herbicidal action

In a greenhouse, immediately after sowing the test plants in seed trays,the surface of the soil is treated with an aqueous dispersion of theactive ingredients obtained from a 25% emulsifiable concentrate.Concentrations of 4 kg of active ingredient/hectare are used. The seedtrays are kept in a greenhouse at 22°-25° C. and 50-70% relativehumidity and the test is evaluated after 3 weeks and the condition ofthe plants is assessed in accordance with the following scale.

1 plant dead or not germinated

2-4 severe damage

5 medium damage, plant remains withered

6-8 slight damage

9 plant growing normally, as untreated control plants

The results of this test are recorded in the following Table:

    ______________________________________                                        compound                                                                      application                                                                            1.27            1.43                                                 rate     1000   500    250  125  1000 500  250  125                           ______________________________________                                        plant                                                                         barley   6      8      9    9    3    4    8    9                             wheat    8      9      9    9    7    8    9    9                             maize    7      7      9    9    5    8    9    9                             rice     4      6      8    9    7    8    9    9                             Avena fatua                                                                            3      6      8    9    1    2    3    7                             Bromus   4      5      7    9    2    4    4    7                             tectorum                                                                      Lolium   2      3      4    7    1    1    1    3                             perenne                                                                       Alopecurus                                                                             1      2      4    5    1    2    4    4                             myosuroides                                                                   Digitaria                                                                              1      1      1    1    1    1    1    1                             sanguinalis                                                                   Echinochloa                                                                            1      1      1    5    1    2    2    4                             crus galli                                                                    Sorghum  1      1      1    7    1    2    5    6                             halepense                                                                     Rottboellia                                                                            1      1      3    7    1    1    2    3                             exaltata                                                                      soybean  7      8      9    9    8    9    9    9                             cotton   7      8      9    9    4    9    9    9                             sunflower                                                                              8      9      9    9    7    8    9    9                             Abutilon 1      1      1    3    1    1    2    4                             Sida     1      2      2    2    1    1    2    2                             spinosa                                                                       Amaranthus                                                                             1      1      1    1    1    1    1    1                             retroflexus                                                                   Chenopodium                                                                            1      1      1    1    1    1    1    1                             Sp.                                                                           Solanum  1      1      1    2    1    1    1    1                             nigrum                                                                        Stellaria                                                                              1      4      6    8    1    1    1    2                             media                                                                         Chrysanthemum                                                                          1      1      4    6    1    2    2    4                             leucum                                                                        Galium   2      2      2    6    2    3    3    7                             apanine                                                                       Viola    1      1      1    1    1    1    1    1                             tricolor                                                                      Veronica Sp.                                                                           1      1      1    1    1    1    1    1                             ______________________________________                                    

EXAMPLE 18 post-emergence herbicidal action (contact herbicide)

A number of weeds, both monocots and dicots, were sprayed afteremergence (at the 4- to 6-leaf stage) with an aqueous dispersion ofactive ingredient at a rate of 4 kg of active ingredient per hectare andkept at 24°-26° C. and 45-60% relative humidity. 15 days after thetreatment, the test is evaluated in accordance with the number scalegiven above. In this test also, the compounds of Tables 1 to 18 exhibita pronounced to very pronounced herbicidal action.

EXAMPLE 19 Herbicidal action before emergence of the plants

Plastics pots are filled with expanded vermiculite (density 0.135 g/cm³,water absorption capacity 0.565 liters/liter). After saturating thenon-adsorptive vermiculite with an aqueous emulsion of active ingredientin deionised water which contains the active ingredients in aconcentration of 70.8 ppm, seeds of the following plants are sown on thesurface: Nasturtium officinalis, Argrostis tenuis, Stellaria media andDigitaria sanguinalis. The test vessels are then kept in a climaticchamber at 20° C., an illumination of about 20 kLux and a relativehumidity of 70%. During the germination phase of 4 to 6 days, the potsare covered with transparent material and watered with deionised waterto increase the local humidity. After the fifth day, 0.5% of acommercially customary liquid fertiliser (^(R) Greenzit) is added to thewater used for watering. 12 days after sowing, the test is evaluated andthe condition of the test plants assessed in accordance with the scalegiven in Example 17.

The results are summarised in the Table below.

    ______________________________________                                        com-                                                                          pound application                                                             no.   rate      Nasturtium                                                                              Agrostis                                                                             Stellaria                                                                            Digitaria                             ______________________________________                                        1.27  100 ppm   1         1      2      1                                            10 ppm   2         1      2      2                                     9.27  100 ppm   1         1      1      1                                            10 ppm   1         1      2      1                                     11.27 100 ppm   2         2      2      2                                     ______________________________________                                    

EXAMPLE 20 Herbicidal action for paddy

The water weeds Echinochloa crus galli and Monocharia vag. are sown inplastics beakers (60 cm² surface area, 500 ml volume). After sowing, thebeakers are filled to the soil surface with water. 3 days after sowing,the water level is raised to slightly above (3-5 mm) the surface of thesoil. Application is carried out by spraying onto the vessels, 3 daysafter sowing, using an aqueous emulsion of the test substances. The dosewhich is therefore used corresponds to a quantity of active ingredientof from 0.5 to 4 kg active ingredient per hectare (spray liquorquantity=550 liters/ha). The plant beakers are then placed in agreenhouse under optimum growth conditions for the rice weeds, i.e. at25°-30° C. and high humidity. The tests are evaluated 3 weeks after theapplication. Compounds of Tables 1 to 18 damage the weeds but not therice.

EXAMPLE 21 Growth inhibition in tropical cover crops

The test plants (cetrosema plumieri and centrosema pubescens) are raiseduntil fully grown and cut back to a height of 60 cm. After 7 days, theactive ingredient is sprayed on in the form of an aqueous emulsion. Thetest plants are kept at 70% relative humidity and 6000 lux artificiallight for 14 hours each day and at a day temperature of 27° and a nighttemperature of 21° C. 4 weeks after the application, the test isevaluated. In evaluating the test, the new growth is estimated andweighed in comparison with the control and the phytotoxicity isassessed. In this test, the plants treated with the active ingredientsof Tables 1 to 18 at application rates of 50-3000 g/ha show a markedreduction in new growth (less than 20% of the new growth in untreatedcontrol plants) without the test plants being at the same time damaged.

EXAMPLE 22 Growth regulation in soybeans

Soybeans of the variety "Hark" are sown in plastics containerscontaining a mixture of soil, peat and sand in a ratio of 6:3:1 andplaced in a climatic chamber. By optimum temperature selection,illumination, application of fertiliser and watering, the plants developafter about 5 weeks to the 5 to 6 trifolia leaf stage. At that time, theplants are sprayed until thoroughly wet with an aqueous liquor of anactive ingredient of the formula I. The active ingredient concentrationis up to 100 g active ingredient/ha. The evaluation is carried out about5 weeks after application of the active ingredient. In comparison withuntreated control plants, the tested active ingredients according to theinvention of Tables 1 to 18 cause a marked increase in the number andweight of the pods in the main shoot.

EXAMPLE 23 Growth inhibition in cereals

Hordeum vulgare (summer barley) and Secale (summer rye) are sown bycereal type in a greenhouse in plastics pots containing sterilised soiland watered as required. About 21 days after sowing, the young shootsare sprayed with an aqueous spray liquor of an active ingredient. Thequantity of active ingredient is up to 100 g of active ingredient perhectare. 21 days after the application, the growth of the cereals isassessed. In comparison with untreated controls, the plants treated withactive ingredients according to the invention show a reduction in newgrowth (60-90% of the control) and in some cases an increase in thediameter of the stalk.

EXAMPLE 24 Growth inhibition in grasses

The grasses Lolium perenne, Poa pratensis, Festuca ovina, Dactylisglomerata and Cynodon dactylon are sown in a greenhouse in plasticstrays containing a soil/peat/sand mixture (6:3:1) and watered asrequired. The emerged grasses are cut back weekly to a height of 4 cmand, about 50 days after sowing and one day after the last cut, sprayedwith an aqueous spray liquor of an active ingredient. The quantity ofactive ingredient is equivalent to up to 500 g of active ingredient perhectare. 21 days after application, the growth of the grasses isassessed.

Tested compounds of Tables 1 to 18 cause a reduction in the new growthof around 10-30% in comparison with the untreated control.

EXAMPLE 25 Desiccating and defoliating action

Cotton plants of the variety Deltapine were raised in clay pots in agreenhouse. When the capsule formation had been completed, they weresprayed with aqueous preparations of an active ingredient at anapplication rate corresponding to 1.2, 0.6 and 0.3 kg/ha in the field.Untreated plants were left as a control. The test was evaluated 3, 7 and14 days after application of the active ingredient by determining thedegree of defoliation (% fallen leaves) and the degree of desiccation (%desiccation of the leaves remaining on the plants).

In this test, on the plants sprayed with compounds of Tables 1 to 18 atapplication rates of 0.6 and 1.2 kg/ha, only a few dried leaves stillremained on the plants after 7 days (>80% leaf fall and desiccation).

We claim:
 1. N-phenylmaleic acid imides of the formula I ##STR102## inwhich R¹ represents hydrogen or fluorine,R² represents halogen, Yrepresents C₁ -C₈ -alkyl, Z represents hydrogen or C₁ -C₈ -alkyl, and Arepresents hydrogen or a group ##STR103## wherein R³ representshydrogen, C₁ -C₄ -alkyl or C₁ -C₄ -haloalkyl, R⁷ represents hydroxy, C₁-C₈ -alkoxy, C₂ -C₈ alkoxyalkoxy, C₂ -C₈ -alkylthioalkoxy, C₃ -C₈-alkenyloxy, C₂ -C₈ -haloalkenyloxy, C₃ -C₈ -alkynyloxy, C₃ -C₇-cycloalkoxy, C₁ -C₈ -alkythio, C₃ -C₈ -alkenylthio, or C₁ -C₄-alkylthio substituted by C₁ -C₈ -alkoxycarbonyl, C₂ -C₈-alkynyloxycarbonyl, C₁ -C₈ -alkylthiocarbonyl, C₃ -C₈-alkenylthiocarbonyl or by C₃ -C₈ -alkynylthiocarbonyl; or C₁ -C₄-alkoxy substituted by C₁ -C₈ -alkoxycarbonyl, C₂ -C₈-alkoxyalkoxycarbonyl, C₃ -C₈ -alkenyloxycarbonyl, C₃ -C₈-alkynloxycarbonyl, C₁ -C₈ alkylthiocarbonyl, C₃ -C₈-alkenylthiocarbonyl, C₃ -C₈ -alkynyltiocarbonyl, R⁸ represents C₁ -C₈-alkyl, C₂ -C₈ -alkoxyalkyl, C₂ -C₈ -alkylthioalkyl, C₂ -C₈ -haloalkyl,C₃ -C₈ -alkenyl, C₃ -C₈ -haloalkenyl, C₃ -C₈ -alkynyl, C₃ -C₇-cycloalkyl, C₁ -C₈ -alkylcarbonyl, allylcarbonyl, phenyl, halophenyl,C₁ -C₄ -alkylphenyl, C₁ -C₄ -alkoxyphenyl, C₁ -C₄ -haloalkylphenyl, C₁-C₄ -haloalkoxyphenyl, nitrophenyl, cyanophenyl, C₁ -C₈ -alkoxycarbonyl,C₂ -C₈ -alkoxyalkoxycarbonyl, C₃ -C₈ -akoxycarbonyl, C₂ -C₈-alkoxyalkoxycarbonyl, C₃ -C₈ -alkenyloxycarbonyl, C₃ -C₈-alkynyloxycarbonyl, C₁ -C₈ -alkyl-thiocarbonyl, C₃ -C₈-alkenylthiocarbonyl or C₃ -C₈ alkynylthiocarbonyl.
 2. A-N-phenylmaleicacid imide according to claim 1 in whichR₁ represents hydrogen orfluorine, R₂ represents chlorine or bromine, Y represents C₁ -C₈ alkyl,Z represents hydrogen or C₁ -C₈ alkyl, A represents the radical --XR⁸and X and R⁸ are as defined in claim
 1. 3. Compounds according to claim1, in whichR¹ represents hydrogen or fluorine, R² represents chlorine orbromine, Y represents C₁ -C₈ -alkyl, Z represents hydrogen or C₁ -C₈-alkyl, A represents the radical --COR³, and R³ represents hydrogen, C₁-C₄ -alkyl or C₁ -C₄ -haloalkyl.
 4. Compounds according to claim 1, inwhichR¹ represents hydrogen or fluorine, R² represents chlorine orbromine, Y represents C₁ -C₈ -alkyl, Z represents hydrogen or C₁ -C₈-alkyl, A represents the radical --COR⁷, and R⁷ is as defined inclaim
 1. 5. N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2,3-dimethylmaleicacid imide according to claim
 1. 6.N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2-n-butyl-3-methyl-maleic acidimide according to claim
 1. 7.N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-3-methyl-2-ethyl-maleic acidimide according to claim
 1. 8.N-(4-chloro-2-fluoro-5-isopropoxyphenyl)-2-ehtyl-3-methyl-maleic acidimide according to claim
 1. 9.N-(4-chloro-2-fluoro-5-isopropoxycarbonylphenyl)-2,3-dimethylmaleic acidimide according to claim
 1. 10. Compounds according to claim 1, inwhichR¹ represents hydrogen or fluorine, R² represents chlorine orbromine, Y and Z each represents methyl, and A has one of the meaningsgiven in claim
 1. 11. Compounds according to claim 1, in whichR¹represents hydrogen or fluorine, R² represents chlorine or bromine, Yrepresents ethyl, Z represents methyl, and A has one of the meaningsgiven in claim
 1. 12. Compounds according to claim 1, in whichR¹represents hydrogen or fluorine, R² represents chlorine or bromine, Yrepresents isopropyl, Z represents methyl, and A has one of the meaningsgiven in claim
 1. 13. Compounds according to claim 1, in whichR¹represents hydrogen or fluorine, R² represents chlorine or bromine, Yrepresents isopropyl, Z represents hydrogen, and A has one of themeanings given in claim
 1. 14. Compounds according to claim 1, inwhichR¹ represents hydrogen or fluorine, R² represents chlorine orbromine, Y represents n-butyl, Z represents methyl, and A has one of themeanings given in claim
 1. 15. A herbicidal and plant growth regulatingcomposition, which contains a herbicidally and growth regulatingeffective amount of an N-phenylmaleic acid imide according to claim 1,together with inert carriers or other additives.
 16. A method forinhibiting the growth of useful plants, which comprises treating theplants with an effective amount of an ingredient according to claim 1 orof a composition containing such an active ingredient.
 17. A method ofcontrolling weeds, which comprises treating the weeds or theirenvironment with an effective amount of a compound according to claim 1or of a composition containing such a compound.
 18. A method accordingto claim 7 of selectively controlling weeds in crops of soybeans,cotton, oats, rye, millet, maize, wheat, barley and rice.